Clemeprol

Clemeprol is an serotonin–norepinephrine reuptake inhibitor antidepressant and anticholinergic agent.
It is an enantiomeric mixture of R and S isomers. Both isomers show similar pharmacological activity.

Synthesis

Published Procedure

A synthetic pathway for clemeprol is disclosed:
The Johnson–Corey–Chaykovsky reaction between 3-chlorobenzophenone and dimethylsulfoxonium methylide, gives 2--2-phenyloxirane . Further reaction with boron trifluoride etherate gives m-chlorophenyl-phenylacetaldehyde, PC12549135. A second Corey-Chaykovsky epoxidation gives 2-oxirane, PC12549073. Quenching with dimethylamine completes the synthesis of clemeprol.

Hypothetical Synthesis

A hypothetical synthesis of clemeprol based on method A in the cited literature is disclosed.
The precursor is called . This would be prepared using methodology that was described already under the diphenylacetonitrile document. A Grignard reaction with one equivalent of methylmagnesium bromide leads to a FGI of the nitrile to the acetyl compound. The alpha-bromination of the acetyl group with one equivalent of a halogenating agent gives. The bromide leaving group is displaced by dimethylamine giving. Sodium borohydride can then be used as the reducing agent to convert the keto carbonyl group into a secondary alcohol, completing the synthesis of clemeprol.