[ CAS No. 28697-17-8 ] {[proInfo.proName]}

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2D 3D

Structure of 28697-17-8 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 28697-17-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 28697-17-8 ]

SDS Specification

Alternatived Products of [ 28697-17-8 ]

Product Details of [ 28697-17-8 ]

CAS No. :	28697-17-8	MDL No. :	MFCD00237380
Formula :	C₁₁H₁₉NO₄	Boiling Point :	-
Linear Structure Formula :	C₅H₉N(COOC(CH₃)₃)COOH	InChI Key :	JQAOHGMPAAWWQO-MRVPVSSYSA-N
M.W :	229.27	Pubchem ID :	688618
Synonyms :		Chemical Name :	(R)-1-(tert-Butoxycarbonyl)piperidine-2-carboxylic acid

Calculated chemistry of [ 28697-17-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.82
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	63.17
TPSA :	66.84 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.41 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.18
Log Po/w (XLOGP3) :	1.82
Log Po/w (WLOGP) :	1.48
Log Po/w (MLOGP) :	1.03
Log Po/w (SILICOS-IT) :	0.5
Consensus Log Po/w :	1.4

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.14
Solubility :	1.65 mg/ml ; 0.00718 mol/l
Class :	Soluble
Log S (Ali) :	-2.84
Solubility :	0.329 mg/ml ; 0.00143 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-0.66
Solubility :	50.7 mg/ml ; 0.221 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.73

Safety of [ 28697-17-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 28697-17-8 ]

* 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 [ 28697-17-8 ]
Downstream synthetic route of [ 28697-17-8 ]

[ 28697-17-8 ] Synthesis Path-Upstream 1~1

1
[ 28697-17-8 ]
[ 688809-99-6 ]

Reference： [1] Patent: WO2012/117048, 2012, A1,

[ 28697-17-8 ] Synthesis Path-Downstream 1~4

1
[ 28697-17-8 ]
[ 134441-61-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With borane-THF; at 0 - 20℃; for 2h;	Compound 2a (5.0 g, 21.8 mmol, 1.0 eq) was dissolved in THF (60 mL),The temperature of the reaction system was lowered to 0 C, BH3.THF (26.2 ml, 26.2 mmol, 1.2 eq) was added to the reaction system, and the temperature was raised to room temperature and stirred for 2 h.The reaction was quenched with saturated NaHCO3 and extracted with EtOAc (2 x 30 mL).It was washed with saturated brine, dried over Na2SO4, and spin-dried to obtain compound 2b (4.8 g, yield: 100%).TLC: DCM / MeOH = 10/1, I2, Rf (compound 2a) = 0.2, Rf (compound 2b) = 0.4.
99%		EXAMPLE 50(b); Starting Material for Examples 50 Et Seq; Step 1; (R)-2-Hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester; To a solution of (R)-Piperidine-1,2-dicarboxylic acid 1-tert-butyl ester (5 g, 21.8 mmol) in anhydrous THF (32 mL) at 0-5 C. was added borane-tetrahydrofuran complex (1M solution in THF) (3.6 g, 41.84 mmol) over a period of 15 min. The mixture was stirred at 0-5 C. for 2 h and then at it for 2 h. The mixture was added over a period of 10 min to cold water (75 mL) and extracted with EtOAc (300 mL). The aqueous layer was re-extracted with EtOAc (2×150 mL). The organic layers were combined, dried over anhydrous Na2SO4 and concentrated to obtain the title product as a colorless oil (4.65 g., 99%).
82%	With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20℃; for 18.25h;	A solution of (R)-1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid (Example 15g,18.5 g, 80.7 mmol) in anhydrous THF (44.4 mL) was cooled to 0C. BH3"Me2S (44.4 mL,88.8 mmol) was added drop wise over 15 minutes. After complete addition, the mixture wasallowed to warm to room temperature, and stirring was continued for 18 hours. The mixturewas quenched with water, and extracted with ethyl acetate. The organic extract was dried15 over anhydrous Na2S04, filtered, and concentrated. The resulting residue was flashchromatographed on silica gel (35% ethyl acetate in hexanes) to provide (R)-tert-butyl-2-(hydroxymethyl)piperidine-1-carboxylate as a white solid (14.2 g, 82%). MS 116 (MH+boc)

Reference： [1]Patent: CN110590747,2019,A .Location in patent: Paragraph 0292-0294
[2]Patent: US2007/66820,2007,A1 .Location in patent: Page/Page column 41
[3]Organic Letters,2004,vol. 6,p. 1813 - 1816
[4]Journal of Medicinal Chemistry,1992,vol. 35,p. 1550 - 1557
[5]Patent: WO2014/25706,2014,A1 .Location in patent: Page/Page column 73

2
[ 28697-17-8 ]
[ 74-88-4 ]
[ 164456-75-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;	Example 1.1; (R)-Piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester; To (R)-Piperidine-1,2-dicarboxylic acid 1-tert-butyl ester (5.1 g, 22.2 mmol) in DMF (60 mL) were added K2CO3 (12.3 g, 88.8 mmol) and Mel (1.7 mL, 26.6 mmol). After stirring at room temperature overnight, the reaction mixture was diluted with ethyl acetate. The organic layer was washed with water (6 times) and brine, dried over anhydrous Na2SO4, filtered and concentrated to give the title product (5.4 g, 99%).1H NMR (300 MHz, CDCl3): delta 4.82 (m, 1H), 3.99 (m, 1H), 3.75 (s, 3H), 2.95 (m, 1H), 2.21 (m, 1H), 2.45 (m, 14H).
99%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;	Example 1.1(R)-Piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester To (R)-Piperidine-1,2-dicarboxylic acid 1-tert-butyl ester (5.1 g, 22.2 mmol) in DMF (60 mL) were added K2CO3 (12.3 g, 88.8 mmol) and MeI (1.7 mL, 26.6 mmol). After stirring at room temperature overnight, the reaction mixture was diluted with ethyl acetate. The organic layer washed with water (6 times) and brine, dried over anhydrous Na2SO4, filtered and concentrated to give the title product (5.4 g, 99%).1H NMR (300 MHz, CDCl3): delta (ppm) 4.82 (m, 1H), 3.99 (m, 1H), 3.75 (s, 3H), 2.95 (m, 1H), 2.21 (m, 1H), 2.45 (m, 14H)
	With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 40℃; for 4.5h;	[0191] To a solution of N-BOC-pipecolinic acid (166.5 g, 726 mmoles) in 500 mL dimethylformamide (DMF) was added MeI (123.7 g, 871 mmoles) and K2CO3 (100.4 g, 726 moles). The reaction mixture slowly exothermed to 40 C. after 0.5 h during a 4 h age period at ambient temperature. Added MTBE (830 mL) and then washed with H2O (2×830 mL) and 20% brine (300 mL). The organic layer was dried over Na2SO4 and concentrated to an oil (3).

With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 20 - 40℃; for 4.5h;

PREPARATIVE EXAMPLE 3; To a solution of N-BOC-pipecolinic acid (166.5 g, 726 mmoles) in 500 mL dimethylformamide (DMF) was added MeI (123.7 g, 871 mmoles) and K2CO3 (100.4 g, 726 moles). The reaction mixture slowly exothermed to 40 C. after 0.5 h during a 4 h age period at ambient temperature. Added MTBE (830 mL) and then washed with H2O (2×830 mL) and 20% brine (300 mL). The organic layer was dried over Na2SO4 and concentrated to an oil (3).

Reference： [1]Patent: US2007/259916,2007,A1 .Location in patent: Page/Page column 9
[2]Patent: US2007/259862,2007,A1 .Location in patent: Page/Page column 10
[3]Patent: US2004/198701,2004,A1 .Location in patent: Page/Page column 10
[4]Patent: US2005/227969,2005,A1 .Location in patent: Page/Page column 10

3
[ 186581-53-3 ]
[ 28697-17-8 ]
[ 164456-75-1 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 5006 - 5009
[2]Organic Letters,2012,vol. 14,p. 5010 - 5013

4
[ 164456-75-1 ]
[ 28697-17-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 184 - 187

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Isomers

Technical Information

? Acyl Group Substitution ? Arndt-Eistert Homologation ? Bouveault-Blanc Reduction ? Catalytic Hydrogenation ? Complex Metal Hydride Reductions ? Ester Cleavage ? Hunsdiecker-Borodin Reaction ? Passerini Reaction ? Preparation of Amines ? Preparation of Carboxylic Acids ? Reactions of Amines ? Reactions of Carboxylic Acids ? Reactions with Organometallic Reagents ? Schmidt Reaction ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Ugi Reaction

Historical Records

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[ 28697-17-8 ]

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[ CAS No. 28697-17-8 ] {[proInfo.proName]}

Quality Control of [ 28697-17-8 ]

Related Doc. of [ 28697-17-8 ]

Product Details of [ 28697-17-8 ]

Calculated chemistry of [ 28697-17-8 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 28697-17-8 ]

Application In Synthesis of [ 28697-17-8 ]

[ 28697-17-8 ] Synthesis Path-Upstream 1~1

[ 28697-17-8 ] Synthesis Path-Downstream 1~4

Technical Information

Related Functional Groups of [ 28697-17-8 ]

Amino Acid Derivatives

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 28697-17-8 ]