Ammonium Chloride → (S)-N-[[3-[3-Fluoro-4-[3-(3-hydroxypropyl)-1H-pyrrol-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Participants

Reaction Steps

A solution of 275 mg (0.66 mmol) of the compound of Example 24 in 15 mL THF was treated with 287 mg (13.2 mmol) of lithium borohydride followed by stirring at ambient temperature for 18 h. The solution was treated with 1 mL of saturated ammonium chloride solution, diluted with ethyl acetate, and extracted with water (3×). Drying (Na2SO4) and concentration in vacuo afforded an oil, which was chromatographed over 20 g of 230-400 mesh silica gel eluting with 2-4% (v/v) methanol in dichloromethane. These procedures afforded 96 mg (39%) of the title compound as a white solid. 1H NMR (CDCl3) δ 7.74, 7.66, 7.38, 7.27, 7.18, 6.95, 6.61, 5.98, 4.82, 4.37, 4.27, 4.09, 3.83, 3.68, 2.88, 2.82, 2.62, 2.04, 1.79.

Provenance & Evidence