tert-Butanol → tert-Butyl cyclohex-3-en-1-ylcarbamate

Participants

Reaction Steps

3-Cyclohexene-1-carboxylic acid (25.3 g) was dissolved in tert-butanol (250 mL), and to the solution were added triethylamine (28 mL) and diphenylphosphoryl azide (43.0 mL), followed by stirring at room temperature for 1 hour, and then at 90° C. for 2 days. The solvent was distilled away under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride). The purified product was further purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to thereby give the title compound (24.9 g).

Provenance & Evidence