Boron tribromide → Nabilone

Participants

Reaction Steps

A solution of dl-trans-1-methoxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-one (prepared as described in Example 1) and boron tribromide in dichloromethane is stirred for about eight hours at about 40° C. The reaction mixture is then washed with water, dried, and the solvent is removed by evaporation under reduced pressure to give dl-trans-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-one. This compound is known as nabilone and is especially useful in the treatment of nausea in humans.

Provenance & Evidence