1-Chloroethyl chloroformate → 5,6,7,8-tetrahydro-4H-furo[3,2-d]azepine

Participants

Reaction Steps

A solution of 6-benzyl-5,6,7,8-tetrahydro-4H-furo[3,2-d]azepine (11.3 mmol) in methylene chloride (56 mL) is cooled to ° C. and treated with 1-chloroethyl chloroformate (ACE-Cl) (56.4 mmol). The reaction is warmed to RT for 1 hour, diluted with methylene chloride (100 mL), washed with NaHCO3 (50 mL), and extracted with methylene chloride (50 mL). The combined organic layers are washed with brine (50 mL), dried and concentrated to give an oily residue which was dissolved in methanol (150 mL) and refluxed for 1 hour. The solvent is removed in vacuo and the crude product is triturated in ether and filtered to give 5,6,7,8-tetrahydro-4H-furo[3,2-d]azepine, which is used without further purification.

Provenance & Evidence