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Quality Control of [ 638-10-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 638-10-8 ]

Product Details of [ 638-10-8 ]

CAS No. :	638-10-8	MDL No. :	MFCD00009187
Formula :	C₇H₁₂O₂	Boiling Point :	-
Linear Structure Formula :	(CH₃)₂CCHCOOCH₂CH₃	InChI Key :	UTXVCHVLDOLVPC-UHFFFAOYSA-N
M.W :	128.17	Pubchem ID :	12516
Synonyms :

Safety of [ 638-10-8 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P210-P403+P235	UN#:	3272
Hazard Statements:	H225	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 638-10-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 638-10-8 ]
Downstream synthetic route of [ 638-10-8 ]

[ 638-10-8 ] Synthesis Path-Upstream 1~1

1
[ 638-10-8 ]
[ 85532-40-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: With ammonia In ethanol at -20 - 90℃; for 24 h; Stage #2: With hydrogenchloride In 1,4-dioxane; ethanol at 20℃; for 0.5 h;	A solution of ethyl 3-methylbut-2-enoate (1 g, 7.8 MMOL) in anhydrous ethanol (12 mL) was cooled to-20 °C and saturated with gaseous ammonia. The tube was sealed and kept at 90°C for 24 hours. The reaction was cooled to room temperature, bubbled with nitrogen to eliminate the residual ammonia and treated with a 4 N solution of HCI in dioxane (1. 9 mL). After 30 minute stirring, the mixture was evaporated under reduced pressure to give ethyl 3- amino-3-methylbutanoate hydrochloride as a grey solid (1.19 G, Y=84percent). 'H NMR (CI3/400 MHz) 5 ppm 1.2 (t, 3H), 1.26 (s, 6H), 2. 65 (s, 2H), 4.1 (q, 2H), 8.27 (BS, 3H).
84%	With ammonia In ethanol at -20 - 90℃; for 24 h;	Example 5 Preparation of 6, 6-DIMETHYL-2, 4-DIOXOPIPERIDINE A solution of ethyl 3-METHYLBUT-2-ENOATE (1 g, 7.8 MMOL) in anhydrous ethanol (12 mL) was cooled to-20 °C and saturated with gaseous ammonia. The tube was sealed and kept at 90°C for 24 hours. The reaction was cooled to room temperature, bubbled with nitrogen to eliminate the residual ammonia and treated with a 4 N solution of HCI in dioxane (1.9 mL). After 30 minute stirring, the mixture was evaporated under reduced pressure to give ethyl 3- AMINO-3-METHYLBUTANOATE HYDROCHLORIDE as a grey solid (1.19 g, Y=84percent).
84%	Stage #1: With ammonia In ethanol at 90℃; for 24 h; Stage #2: With hydrogenchloride In 1,4-dioxane; ethanol for 0.5 h;	EXAMPLE 7 Preparation of 6,6-dimethyl-2,4-dioxopiperidine A solution of ethyl 3-methylbut-2-enoate (1 g, 7.8 mmol) in anhydrous ethanol (12 mL) was cooled to -20° C. and saturated with gaseous ammonia. The tube was sealed and kept at 90° C. for 24 hours. The reaction was cooled to room temperature, bubbled with nitrogen to eliminate the residual ammonia and treated with a 4 N solution of HCl in dioxane (1.9 mL). After 30 minute stirring, the mixture was evaporated under reduced pressure to give ethyl 3-amino-3-methylbutanoate hydrochloride as a grey solid (1.19 g, Y=84percent). ¹H NMR (CDCl₃/400 MHz) δ ppm 1.2 (t, 3 H), 1.26 (s, 6 H), 2.65 (s, 2 H), 4.1 (q, 2 H), 8.27 (bs, 3 H).

70%	Stage #1: With ammonia In ethanol at 90℃; for 24 h; Stage #2: With hydrogenchloride In 1,4-dioxane at 20℃; for 0.5 h;	INTERMEDIATE 49Ethyl 3-ammo-3-methylbutanoate hydrochloride; To a stirred solution of ethyl 3,3-dimethylacrylate (5.0 g, 39.1 mmol) in EtOH (20 mL) in a Parr.(R). reactor at O⁰C was added liquid NH₃ (approximately 20 mL). The reactor was sealed and heated to 9O⁰C for 24 h. The reaction mixture was then cooled to r.t., bubbled with nitrogen to remove the residual NH₃ and treated with 4M HCl in 1 ,4- dioxane (10 mL). The reaction mixture was stirred for 30 minutes at r.t. and then evaporated in vacuo to dryness. The resulting grey paste was triturated with DCM, filtered and dried to give the title compound (5.0 g, 70percent) as a grey solid that was used without further purification. δ_H (CDCl₃) 8.27 (3H, br. s), 4.10 (2H, q, J7.1 Hz), 2.65 (2H, s), 1.26 (6H, s), 1.20 (3H, t, J 7.1 Hz).
70%	Stage #1: With ammonia In ethanol at 0 - 90℃; for 24 h; Stage #2: With hydrogenchloride In ethanol at 20℃; for 0.5 h;	INTERMEDIATE 1Ethyl 3-amino-3-methylbutanoate hydrochlorideTo a stirred solution of ethyl 3,3-dimethylacrylate (5.0 g, 39.1 mmol) in EtOH (20 mL) in a Parr^.(R). reactor at 0⁰C was added liquid NH₃ (ca 20 mL). The reactor was sealed and heated to 90⁰C for 24 h. The reaction mixture was then cooled to r.t., bubbled with nitrogen to remove the residual NH₃ and treated with 4M HCl in dioxane (10 mL). The reaction mixture was stirred for 30 minutes at r.t. and then evaporated in vacuo to dryness. The resulting grey paste was triturated with DCM, filtered and dried to give the title compound (5.0 g, 70percent) as a grey solid that was used without further purification. 6_H (CDCl₃) 8.27 (3H, br. s), 4.10 (2H, q, J7.1 Hz), 2.65 (2H, s), 1.26 (6H, s), 1.20 (3H, t, J 7.1 Hz).
70%	Stage #1: With ammonia In ethanol at 0 - 90℃; for 24 h; Stage #2: With hydrogenchloride In 1,4-dioxane; ethanol at 20℃; for 0.5 h;	INTERMEDIATE 1Ethyl 3-amino-3-methylbutanoate hydrochlorideTo a stirred solution of ethyl 3,3-dimethylacrylate (5.0 g, 39.1 mmol) in EtOH (20 mL) in a Parr.(R). reactor at O⁰C was added liquid NH₃ (ca 20 mL). The reactor was sealed and heated to 9O⁰C for 24 h. The reaction mixture was then cooled to r.t, bubbled with nitrogen to remove the residual NH₃ and treated with 4M HCl in 1 ,4-dioxane (10 mL). The reaction mixture was stirred for 30 minutes at r.t. and then evaporated in vacuo to dryness. The resulting grey paste was triturated with DCM, filtered and dried (MgSO₄) to give the title compound (5.0 g, 70percent) as a grey solid that was used without further purification. δ_H (CDCl₃) 8.27 (3H, br s), 4.10 (2H, q, J 7.1 Hz), 2.65 (2H, s), 1.26 (6H, s), 1.20 (3H, t, J7.1 Hz).
70%	Stage #1: With ammonia In ethanol at 0 - 90℃; for 24 h; Stage #2: With hydrogenchloride In 1,4-dioxane; ethanol at 20℃; for 0.5 h;	To a stirred solution of ethyl 3,3-dimethylacrylate (5.0 g, 39.1 mmol) in EtOH (20 mL) in a PARR.(R). reactor was added liquid NH₃ (ca 20 mL) at 0⁰C. The reactor was sealed and heated to 90⁰C for 24 h. The reaction mixture was then cooled to r.t., bubbled with N₂ to remove the residual NH₃ and treated with 4M HCl in 1,4-dioxane (10 mL). The reaction mixture was stirred for 30 minutes at r.t. and then evaporated in vacuo to dryness. The resulting grey paste was triturated with DCM, filtered and dried to give the title compound as a grey solid (5.0 g, 70percent) that was used without further purification. 5_H (CDCl₃) 8.27 (3H, br. s), 4.10 (2H, q), 2.65 (2H, s), 1.26 (6H, s), 1.20 (3H, t).
58.8%	Stage #1: With ammonia In ethanol at -70 - 45℃; for 16 h; Autoclave Stage #2: With hydrogenchloride In 1,4-dioxane at 0℃; for 0.5 h; Inert atmosphere	Step II-I-a: Ethyl 3-amino-3-methylbutanoate hydrochloride salt (11-I-a)To a solution of ethyl 3-methylbut-2-enoate (15 g, 117 mmol) in EtOH (40 mL) was added liquid ammonia (80 mL) at -70° C. and the reaction mixture stirred in a autoclave (200 Psi) at 45° C. for 16 h. After completion of the reaction (monitored by TLC), excess ammonia was removed by flashing N₂, cooled to 0° C. and HCl in dioxane (pH-2) was added. The reaction mixture was stirred for 30 minutes at 0° C., the volatiles were removed under reduced pressure and the obtained solid was washed with diethyl ether to afford 11-I-a-HCl salt (10 g, 58.8percent) as white solid; TLC: 10percent MeOH/DCM (R_f: 0.1); ¹H-NMR (DMSO d₆, 200 MHz): δ 8.33 (bs, 1H), 4.09 (q, J=7.0 Hz, 2H), 2.70 (s, 2H), 1.33 (s, 6H), 1.20 (t, J=7.0 Hz, 3H); Mass: 146 [M⁺+1].
58.8%	With hydrogenchloride; ammonia In 1,4-dioxane; ethanol	Step 5-I-a: Ethyl 3-amino-3-methylbutanoate hydrochloride salt (5-I-a) To a solution of ethyl 3-methylbut-2-enoate (15 g, 117 mmol) in EtOH (40 mL) was added liquid ammonia (80 mL) at -70° C. and the reaction mixture stirred in a autoclave (200 Psi) at 45° C. for 16 h. After completion of the reaction (monitored by TLC), excess ammonia was removed by flashing N₂, cooled to 0° C. and HCl in dioxane (pH?2) was added. The reaction mixture was stirred for 30 minutes at 0° C., the volatiles were removed under reduced pressure and the obtained solid was washed with diethyl ether to afford 5-I-a-HCl salt (10 g, 58.8percent) as white solid; TLC: 10percent MeOH/DCM (R_f: 0.1); ¹H-NMR (DMSO d₆, 200 MHz): δ 8.33 (bs, 1H), 4.09 (q, J=7.0 Hz, 2H), 2.70 (s, 2H), 1.33 (s, 6H), 1.20 (t, J=7.0 Hz, 3H); Mass: 146 [M⁺+1].

Reference： [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 2, p. 293 - 307
[2] Patent: WO2005/13986, 2005, A1, . Location in patent: Page/Page column 36
[3] Patent: WO2005/14572, 2005, A1, . Location in patent: Page/Page column 26; 27
[4] Patent: US2007/142414, 2007, A1, . Location in patent: Page/Page column 17
[5] Patent: WO2008/20206, 2008, A2, . Location in patent: Page/Page column 50
[6] Patent: WO2009/1089, 2008, A1, . Location in patent: Page/Page column 22
[7] Patent: WO2009/71895, 2009, A1, . Location in patent: Page/Page column 94
[8] Patent: WO2009/71888, 2009, A1, . Location in patent: Page/Page column 71
[9] Patent: US2011/230476, 2011, A1, . Location in patent: Page/Page column 291-292
[10] Patent: US2011/269244, 2011, A1, . Location in patent: Page/Page column
[11] Patent: US2011/3785, 2011, A1, . Location in patent: Page/Page column 8-9

[ 638-10-8 ] Synthesis Path-Downstream 1~5

1
[ 638-10-8 ]
[ 100-46-9 ]
[ 17945-54-9 ]

Yield	Reaction Conditions	Operation in experiment
21%	In ethanol; for 24.0h;Heating / reflux;	Step 1 Ethyl 3-benzylamino-3-methylbutyrate A solution of ethyl 3,3-dimethylacrylate (19.3 g, 0.151 mol) in EtOH (150 mL) was added benzylamine (16.2 g, 0.151 mol) and refluxed for 24 h. The reaction mixture was concentrated in vacuo. The distillation of the residue gave ethyl 3-benzylamino-3-methylbutyrate as a colorless oil (7.48 g, 21%). 1H-NMR (400 MHz, CDCl3) delta 1.24 (6H, s), 1.26 (3H, t, J=7.3 Hz), 2.51 (2H, s), 3.72 (2H, s), 4.14 (2H, q, J=7.3 Hz), 7.20-7.38 (5H, m).

Reference： [1]Patent: US2007/254866,2007,A1 .Location in patent: Page/Page column 102
[2]Journal of Organic Chemistry,1968,vol. 33,p. 1322 - 1333

2
[ 638-10-8 ]
[ 101166-65-8 ]
[ 916991-65-6 ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 8267 - 8270

3
[ 638-10-8 ]
[ 130985-42-1 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 633 - 642

4
[ 638-10-8 ]
[ 488-10-8 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1990,p. 684 - 686

5
[ 638-10-8 ]
[ 21883-13-6 ]
[ 1239648-19-1 ]

Yield	Reaction Conditions	Operation in experiment
59%		General procedure: A dry round bottom flask was charged with anhydrous diglyme (24 mL) and diisopropylamine (2.91 mL, 20.4 mmol), then cooled to -78 C in a dry ice/acetone bath. To this solution was added n-butyllithium (2.5 M in hexanes, 8.15 mL, 20.4 mmol). The reaction was removed from the dry ice/acetone bath for 10 min, then re-cooled to -78 C. The desired o-tolunitrile 9a-d (6.79 mmol), dissolved in anhydrous diglyme (2 mL), was then added slowly dropwise then allowed to stir at -78 C for 45 min. (0048) A separate dry flask was charged with anhydrous diglyme (8.0 mL) and zinc powder (1.11 g, 17.0 mmol). Molecular iodine (3.45 g, 13.6 mmol) was added portionwise over the course of 10 min. The suspension was subsequently heated via heat gun in 30-s intervals until a silver precipitate of ZnI2 had formed and all iodine color had disappeared (caution: exothermic). (0049) Ethyl-3,3-dimethyl acrylate (1.42 mL, 10.2 mmol) was added to the first flask dropwise over 10 min. The flask containing the ZnI2 suspension was then added to the reaction vessel and the resulting suspension allowed to stir for an additional 2 h, slowly warming to room temperature. The reaction was quenched by the addition of saturated ammonium chloride solution and the resulting biphasic suspension was extracted with diethyl ether (3 × 30 mL), then washed with water (4 × 50 mL) and brine (1 × 50 mL). The organic extract was dried over MgSO4, vacuum filtered, and concentrated in vacuo. Further purification via flash chromatography (silica gel, 5% EtOAc/hex) delivered the desired 10a-d in 33-59% yields.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 1880 - 1897

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H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 638-10-8 ] {[proInfo.proName]}

Quality Control of [ 638-10-8 ]

Related Doc. of [ 638-10-8 ]

Product Details of [ 638-10-8 ]

Safety of [ 638-10-8 ]

Application In Synthesis of [ 638-10-8 ]

[ 638-10-8 ] Synthesis Path-Upstream 1~1

[ 638-10-8 ] Synthesis Path-Downstream 1~5

Technical Information

Related Functional Groups of [ 638-10-8 ]

Alkenyls

Aliphatic Chain Hydrocarbons

Esters

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 638-10-8 ]