Ammonium Chloride → HCID 15117274, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (7.7 ml) in dichloromethane (200 ml) was added dropwise dimethyl sulfoxide (7.7 ml) at -78° C. After stirring at -78° C. for 20 minutes, to the mixture was added dropwise a solution of 1-allyloxycarbonyl-4-hydroxymethylpiperidine (14 g) in dichloromethane (20 ml). After stirring at -78° C. for 30 minutes, to the mixture was added dropwise triethylamine (35 ml) and the resulting mixture was allowed to stir at 0° C. The solution was washed with brine and dried. Evaporation of the solvent gave an oil, which was dissolved in tetrahydrofuran (100 ml). To the solution was added 1N-ethylmagnesium bromide in tetrahydrofuran solution (35 ml) at 0° C. After stirring for 1 hour at 0° C., to the solution was added saturated aqueous ammonium chloride, and the organic layer was separated. The dried organic layer was evaporated, and the residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (2:1, V/V) to give 1-allyloxycarbonyl-4-(1-hydroxypropyl)piperidine (12.8 g).

Provenance & Evidence