Tetrahydrofuran → (S)-2-(2,4-Difluoro-benzyl)-butan-1-ol

Temperature

0 °C

A flask was charged with 29.5 g (˜78.6 mmol) of (4R,5S)-[(S)-2-(2,4-difluoro-benzyl)-butyryl]-4-methyl-5-phenyl-oxazolidin-2-one and 200 mL of dry THF, and the solution was cooled to 0° C. In a separate flask, 11.9 g (314 mmol) of sodium borohydride was taken up in 70 mL of water and added dropwise over 15 minutes to the imide solution. The mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was quenched with conc. HCl until pH=3 (keeping the reaction mixture temperature <20° C.). THF was removed under reduced pressure, and the residue was taken up in hexanes. The hexane layer was washed with sat. aq. sodium bicarbonate. The hexane layer was removed under reduced pressure, and the residue was purified by column chromatography (9:1 Hexanes/EtOAc) which gave 7.2 g (46% yield) of the titled compound as a clear oil.

1. temperatureto warm to room temperature
2. customThe reaction mixture was quenched with conc. HCl until pH=3 (
3. customthe reaction mixture temperature <20° C.
4. customTHF was removed under reduced pressure
5. washThe hexane layer was washed with sat. aq. sodium bicarbonate
6. customThe hexane layer was removed under reduced pressure
7. customthe residue was purified by column chromatography (9:1 Hexanes/EtOAc) which

ORD record

ord-c332dc16c5174975acc72261f3c22b74

Source dataset

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07388023B2