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A simple, scalable synthetic route to (+)- and (-)-pseudoephenamine.

ABSTRACT: A three-step synthesis of pseudoephenamine suitable for preparing multigram amounts of both enantiomers of the auxiliary from the inexpensive starting material benzil is described. The sequence involves synthesis of the crystalline monomethylimine derivative of benzil, reduction of that substance with lithium aluminum hydride, and resolution of pseudoephenamine with mandelic acid.

SUBMITTER: Mellem KT

PROVIDER: S-EPMC3864801 | biostudies-literature | 2013 Nov

REPOSITORIES: biostudies-literature

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A simple, scalable synthetic route to (+)- and (-)-pseudoephenamine.

Mellem Kevin T KT Myers Andrew G AG

Organic letters 20131018 21

A three-step synthesis of pseudoephenamine suitable for preparing multigram amounts of both enantiomers of the auxiliary from the inexpensive starting material benzil is described. The sequence involves synthesis of the crystalline monomethylimine derivative of benzil, reduction of that substance with lithium aluminum hydride, and resolution of pseudoephenamine with mandelic acid. ...[more]

PMID: 24138164

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