Allyl chloroformate → HCID 15117212, compound

Participants

Reaction Conditions

Reaction Steps

1,4-Diacetyl-4-hydroxypiperidine (0.2 g) was dissolved in 1N hydrochloric acid (4 ml) and the solution was heated at 100° C. for 15 hours. After cooling to 0° C., the reaction mixture was diluted with a mixture of tetrahydrofuran (10 ml) and water (10 ml). To the mixture was added dropwise at 0° C. a solution of allyl chloroformate (0.15 ml) in tetrahydrofuran (2 ml) while adjusting pH to around 10 with aqueous potassium hydride. After stirring at 0° C. for 30 minutes, the reaction mixture was diluted with a mixture of ethyl acetate and water. The organic layer was separated, washed in turn with water and brine, and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (10 g) eluting with a mixture of n-hexane and ethyl acetate (9:1-1:1, V/V) to give 4-acetyl-1-allyloxycarbonyl-4-hydroxypiperidine (0.26 g).

Provenance & Evidence