Ammonium Chloride → HCID 53818593, compound

Participants

Reaction Steps

Using a commercially available piperidine-4-carboxylic acid ethyl ester, (S)-1-{4-[5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-piperidine-4-carboxylic acid ethyl ester (Compound No. 1) was synthesized by the same method as in Example 1. To a THF solution (6.6 ml) of this compound (661 mg), lithium chloride (275 mg), sodium borohydride (245 mg) and ethanol (4.5 ml) were added successively and the mixture was stirred at room temperature for 14 h. A saturated aqueous ammonium chloride solution was added to the reaction solution and the reaction mixture was extracted with methylene chloride; the organic layer was washed with water and brine, dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (solvent: chloroform/methanol=25/1-15/1) to afford the title compound (402 mg) in a yield of 68%.

Provenance & Evidence