* 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.
Reference:
[1] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 19, p. 2253 - 2258
[2] Synlett, 2002, # 12, p. 2039 - 2040
[3] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 2, p. 576 - 585
2
[ 159877-47-1 ]
[ 167216-17-3 ]
Yield
Reaction Conditions
Operation in experiment
1.3 g
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at -78℃; for 1 h; Inert atmosphere Stage #2: With sodium hydroxide In water at 20℃; for 1 h;
To a solution of (R)-3-((tert-butoxycarbonyl)amino)butanoate (3.0 g, 14.76 mmol) in tetrahydrofuran (THF) (50 mL) was added aluminum(III) lithium hydride (0.728 g, 19.19 mmol), stirred at -78 °C for 1 h under nitrogen. The reaction mixture was warmed to 0°C, quenched by addition of H20 (0.7 mL) and aq. 15percent NaOH (0.7 mL), stirred for 1 h at r.t, filtered through celite, dried over Na2S04, concentrated to afford the title compound (1.3 g).
Reference:
[1] Advanced Synthesis and Catalysis, 2010, vol. 352, # 1, p. 92 - 96
[2] Patent: US2011/237814, 2011, A1, . Location in patent: Page/Page column 11
[3] Patent: WO2014/114249, 2014, A1, . Location in patent: Page/Page column 21
With dmap; triethylamine; In tetrahydrofuran; at 25℃;Inert atmosphere;
NHBoc To a solution of (R)-methyl 3-aminobutanoate (1.3 g, 1 1.10 mmol), TEA (4.64 mL, 33.3 mmol) and N,N-dimethylpyridin-4-amine (0.136 g, 1.1 10 mmol) in tetrahydrofuran (THF) (40 mL) was added di-tert-butyl dicarbonate (3.63 g, 16.65 mmol), stirred at stirred at 25 C for overnight under nitrogen. The organic phase was washed with brine, dried over sodium sulphate to afford the title compound (3.0 g).
With hydrogen;carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)amino]ruthenium(II); In tetrahydrofuran; at 80℃; under 37503.8 Torr; for 16h;Inert atmosphere;
Example 5Hydrogenation of methyl(R)-3-(Boc-amino)butanoate was carried out according to the following reaction scheme. The complex 1b (0.02 mmol) produced in Example 1 was added to a 100 mL autoclave equipped with a stirrer and purged with nitrogen gas. Tetrahydrofuran (4 mL) and methyl (R)-3-(Boc-amino)butanoate (5 mmol) with 99% ee or higher were added thereto, and the hydrogenation was carried out at 80 C. for 16 hrs with hydrogen pressure of 5 MPa. As a result of the analysis of the reaction solution according to gas chromatography, it was found that (R)-3-(Boc-amino)butan-1-ol was obtained with the conversion rate of 95.9%. Optical purity of the alcohol obtained was 99% ee or higher.
1.3 g
To a solution of (R)-3-((tert-butoxycarbonyl)amino)butanoate (3.0 g, 14.76 mmol) in tetrahydrofuran (THF) (50 mL) was added aluminum(III) lithium hydride (0.728 g, 19.19 mmol), stirred at -78 C for 1 h under nitrogen. The reaction mixture was warmed to 0C, quenched by addition of H20 (0.7 mL) and aq. 15% NaOH (0.7 mL), stirred for 1 h at r.t, filtered through celite, dried over Na2S04, concentrated to afford the title compound (1.3 g).