Cypenamine - Stereochemistry

Stereochemistry

2-Phenylcyclopentan-1-amine is a compound with two stereocenters. Thus, the following four following stereoisomers may exist:

  • (1R,2S)-trans-2-phenylcyclopentan-1-amine
  • (1S,2R)-trans-2-phenylcyclopentan-1-amine
  • (1R,2R)-cis-2-phenylcyclopentan-1-amine
  • (1S,2S)-cis-2-phenylcyclopentan-1-amine

The racemate (±)-trans-2-phenylcyclopentan-1-amine is the active ingredient of cypenamine. Furthermore, the kinetic resolution of (±)-trans-2-phenylcyclopentan-1-amine by lipase B from Candida antarctica may effectivily performed by an aminolysis reaction.

Racemic cis-2-phenylcyclopentan-1-amine has found no pharmacological application.

Read more about this topic:  Cypenamine

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