Ethanol → 1,1-Dimethylethyl N-[(1S,3R)-4-hydroxy-1-(hydroxymethyl)-3-methylbutyl]carbamate
Reaction equation
[CH3:1][C@H:2]1[C:6](=[O:7])[N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@H:4]([C:15](OC)=[O:16])[CH2:3]1.[BH4-].[Na+].CCO>C1COCC1.CCOC(C)=O>[OH:7][CH2:6][C@H:2]([CH3:1])[CH2:3][C@H:4]([NH:5][C:8](=[O:9])[O:10][C:11]([CH3:13])([CH3:12])[CH3:14])[CH2:15][OH:16]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -10 °C
Procedure
To a solution of 1-tert-butyl 2-methyl (2S,4R)-4-methyl-5-oxopyrrolidine-1,2-dicarboxylate (0.47 g, 1.8 mmol) in THF (4.0 mL) at −10° C., NaBH4 (0.207 g, 5.48 mmol) was added followed by EtOH (1.0 mL). After stirring at −10° C. for 1 h, the mixture was allowed to warm to room temperature and stirred for 15 h. The reaction mixture was then diluted with EtOAc (50 mL), washed with water (25 mL) and brine (30 mL), then dried over Na2SO4 and concentrated under reduced pressure. The resulting crude product (0.39 g, 92%) was used directly in the next step without further purification. LCMS calc. for C11H24NO4 (M+H)+: m/z=234.2. found no ionization.
Workup
- temperatureto warm to room temperature
- stirringstirred for 15 h
- washwashed with water (25 mL) and brine (30 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
- customThe resulting crude product (0.39 g, 92%) was used directly in the next step without further purification
Sources & evidence
- ORD record
- ord-5bbbbad3368a469ca3476b39d2b5aaf3
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09278950B2
Reaction notes
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