Triethylamine → HCID 15117273, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-allyloxycarbonyl-4-carboxypiperidine (37 g) in tetrahydrofuran (400 ml) were added triethylamine (31 ml) and isobutyl chloroformate (27 ml) at -30° C. After stirring for 30 minutes at 0° C., the precipitate was filtered off. The obtained solution was added dropwise to the solution of sodium borohydride (13 g) in water (100 ml) at 0° C. After stirring for 1 hour at 0° C., sodium chloride was added to saturate the aqueous layer, and the organic layer was separated. The dried organic layer was evaporated and then the residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (1:1-1:2, V/V) to give 1-allyloxycarbonyl-4-hydroxymethylpiperidine (24 g).

Provenance & Evidence