Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | ||||||
{[ item.p_purity ]} | {[ item.pr_size ]} | Inquiry |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price) ]} |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]} | {[ item.pr_usastock ]} | in stock Inquiry - | {[ item.pr_chinastock ]} | {[ item.pr_remark ]} in stock Inquiry - | Login | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
CAS No. : | 161344-84-9 | MDL No. : | MFCD05663838 |
Formula : | C12H23BN2O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | AFQWQRBBIZKYTE-UWVGGRQHSA-N |
M.W : | 270.13 | Pubchem ID : | 10978509 |
Synonyms : |
|
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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; water; at 20℃; for 1.0h; | Example 26B; 2-Butyl-f 1.3.21dioxaborolane-(S.S)-4.5-dicarboxylic acid bis-dimethylamide; 2-(But-1-yl)-tetrahydro-4H-1,3,6,2-dioxazaborocine [CAS 92527-13-4] was prepared from n-butylboronic acid and 2-(2-hydroxy-ethylamino)-ethanol [CAS 111-42-2] as reported in Organic Synthesis, 1998, 76, 86-96. This dioxazaborocine (3 g, 17.5 mmol) and (2S,3S)-2,3-dihydroxy-N,N,N',N'- tetramethyl-butanediamide [CAS 63126-52-3] (4.65 g) were dissolved in anhydrous dichloromethane (95 ml.) under N2. Brine (30 ml_) was added. The resulting mixture was stirred at room temperature for 1 hour. The two layers were separated, and the aqueous layer was extracted with dichloromethane (30 ml_). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to provide the title compound as an oil. 1H NMR (300 MHz, CDCI3): delta 0.82-0.9 (m, 5H), 1.25-1.45 (m, 4H), 2.98 (s, 6H), 3.2 (s, 6H), 5.52 (S, 2H). MS (DCI-NH3) m/z 271 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.41 g (91%) | In hexane; dichloromethane; ethyl acetate; | 4,4-Dimethyl-6-[(1S,2S)-3-hydroxy-1,2-methano-1-methyl-propyl]-2-oxo-1-(2-propyl)-1,2,3,4-tetrahydroquinoline Compound 11 To a stirred, cooled (-25 C.) solution of diethyl zinc in anhydrous dichloromethane (9.06 mL, 16.4 mmol) under argon, 1,2-dimethoxyethane (1.7 mL, 16.4 mmol) was added over 2 minutes followed by diiodomethane (2.7 mL, 32.8 mmol) at such a rate that the temperature of the cooling bath did not increase above -20 C. After the addition was complete, the reaction mixture was stirred for 5 minutes and then cannulated into a cooled (-25 C.), stirred solution of 4,4-dimethyl-6-(3-hydroxy-1-methyl-prop-1(Z)-enyl)-2-oxo-1-(2-propyl)-1,2,3,4-tetrahydroquinoline (Compound 9 0.43 g, 1.5 mmol), 4A molecular sieves powder (0.5 g) and (4S-trans)-2-butyl-N,N,N',N'-tetramethyl[1,3,2]dioxaborolane-[4,5]dicarboxamide (Compound 10) in 10 mL of anhydrous dichloromethane over 5 minutes. The slurry was stirred at -25+ C. for 1.5 hour, at -15 C. for 3 hours and at 0 C. for 3 hours. The reaction was quenched with 20 mL of saturated, aqueous ammonium chloride solution and extracted with dichloromethane (2*35 mL). The combined organic extract was dried over anhydrous sodium sulfate and the solvent evaporated to give a residue which on purification by flash column chromatography on silica gel (230-400 mesh) using 30% ethyl acetate in hexane as the eluent provided 0.41 g (91%) of the title compound as a pale yellow, viscous oil. 1 H-NMR (300 MHz, CDCl3):d 0.78-0.86(m, 2H), 1.20-1.30(m, 1H), 1.27(s, 6H), 1.39(s, 3H), 1.53(d, J=7.0 Hz, 6H), 2.40(s, 2H), 3.25(dq, J=11.4 Hz, 2H), 4.64(heptet, J=7.0 Hz, 1H), 7.04(d, J=8.4 Hz, 1H), 7.17(dd, J=8.3, 2.0 Hz, 1H), 7.22(d, J=2.0 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Dichloromethane stabilized with EtOH was distilled from CaH2 under N2 and sparged with N2 to maintain oxygen free solvents.A 500 ml 3N round bottom flask was equipped with an addition funnel topped with a 3 way stopcock and internal thermal couple. The apparatus was evacuated and backfilled with N2 4 times. To this degassed vessel was added 20 mL DCM, Diethyl Ether (5.06 g, transferred by weight) and a solution OfEt2Zn (8.43 g, 68.2 mmol, in 30 ml DCM) under a N2 atmosphere. The solution was cooled to -20 C and a solution Of CH2I2 (36.5 g, 136 mmol, in 20 ml DCM) was added dropwise. The temperature is monitored with an internal temperature probe. The rate of addition was altered to maintain a constant -20 C internal temperature. A fine precipitate forms after the addition is -80% complete. The mixture was stirred for 10 minutes.A solution of the commercially available (S, S) dioxaborolane Hgand (7.37 g, 27.3 mmol) in DCM (20 mL) was added. The mixture was stirred for 10 minutes. The precipitate dissolves yielding a clear solution. A solution of the alkene from step 2 of this example (8.53 g, 22.7 mmol) in DCM (20 mL) was added. The solution was warmed to 0 C and stirred for 24 hours. The solution remains clear after stirring for 24 hours. The reaction was quenched after 24 hr by addition of 50 ml of sat'd aq. NH4Cl. The mixture was placed in a separatory funnel, 250 ml DCM and 200 ml 10 % HCl (aq) added, shaken, and the layers separated. The aqueous layer was re-extracted with DCM (2 x 150ml), the organic layers combined, transferred to a Morton flask. 2N NaOH (300 ml) and 50 ml of 30% H2O2 were added. The biphasic solution was stirred vigorously for 12 hours. The layers were separated and the aqueous phase was re-extracted with DCM (2 x 150ml), the organic phases were combined, washed with 10% HCl (aq, 250 ml), IN Na2S2O3 (250 ml), sat'd NaHCO3 (250 ml), brine (250 ml), dried over MgSO4, filtered and stripped. The material was purified by chromatography on SiO2 eluting with 30% EtOAc : Hexanes. The desired product is obtained as a mixture with the minor diastereomer and the residual SM. The desired diastereomer was isolated by chromatography on Chiralpak IA stationary phase. |
[ 161344-85-0 ]
2-Butyl-[1,3,2]dioxaborolane-4,5-dicarboxylicacidbis-dimethylamide
Similarity: 1.00
[ 161344-85-0 ]
2-Butyl-[1,3,2]dioxaborolane-4,5-dicarboxylicacidbis-dimethylamide
Similarity: 1.00
[ 161344-85-0 ]
2-Butyl-[1,3,2]dioxaborolane-4,5-dicarboxylicacidbis-dimethylamide
Similarity: 1.00
[ 161344-85-0 ]
2-Butyl-[1,3,2]dioxaborolane-4,5-dicarboxylicacidbis-dimethylamide
Similarity: 1.00