Tetrahydrofuran → HCID 53866615, compound

Participants

Reaction Steps

To a solution of 3-(3(S)-(3,4-dichlorophenyl)-2(S)-azido-1-oxo-5-hexenyl)-4(S)-benzyl-2-oxazolidinone (890 mg, 1.94 mmol) and THF (25 mL) at 0° C. was added MeOH (126 mL, 3.1 mmoL), followed by LiBH4 (68 mg, 3.1 mmol). The mixture was allowed to stir for 2 h, and was then quenched by addition of sat. aq. Rochelle salts (50 mL) and was allowed to warm to room temp and stirred vigorously for 2 h. The mixture was diluted with H2O (150 mL) and extracted with CH2Cl2 (3×100 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography (silica gel 60, 10-40% EtOAc/hexanes) to afford the alcohol (452 mg, 82%) as a colorless oil.

Provenance & Evidence