Ethanol → (R)-tert-butyl 4-((1R,2S)-1-(tert-butyldimethylsilyloxy)-3-hydroxy-2-methylpropyl)-2,2-dimethyloxazolidine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

LiBH4 (0.25 g, 11 mmol) was added to a mixture of tert-butyl (4R)-4-((1R,2R)-3-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-1-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-3-oxopropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (2.2 g, 3.8 mmol) and EtOH (0.67 mL, 11 mmol) in THF (40 mL) at −30° C. The mixture was allowed to warm to 0° C. and stirred for 3 h. The reaction mixture was then diluted with Et2O and 1 M NaOH was added. The resulting mixture was extracted with EtOAc. The separated organic extract was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluting with 0-20% EtOAc in hexanes) to give the sub-title compound (1.2 g, 78%). LCMS calc. for C15H34NO3Si (M+H-Boc)+: m/z=304.2. found 304.2.

Provenance & Evidence