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Concise route to the chiral pyrrolidine core of selective inhibitors of neuronal nitric oxide.

ABSTRACT: 2-(((3R,4R)-4-(Allyloxy)-1-benzylpyrrolidin-3-yl)methyl)-6-(2,5-dimethyl-1H-pyrrol-1-yl)-4-methylpyridine (2), a key intermediate for the preparation of novel neuronal nitric oxide synthase (nNOS) inhibitors, is synthesized using diisopropyl (R)-(+)-malate as the starting material. The key steps involve a Frater-Seebach diastereoselective alkylation and a fast intramolecular cyclization.

SUBMITTER: Xue F

PROVIDER: S-EPMC2783674 | biostudies-literature | 2009 Nov

REPOSITORIES: biostudies-literature

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Concise route to the chiral pyrrolidine core of selective inhibitors of neuronal nitric oxide.

Xue Fengtian F Gu Wenxin W Silverman Richard B RB

Organic letters 20091101 22

2-(((3R,4R)-4-(Allyloxy)-1-benzylpyrrolidin-3-yl)methyl)-6-(2,5-dimethyl-1H-pyrrol-1-yl)-4-methylpyridine (2), a key intermediate for the preparation of novel neuronal nitric oxide synthase (nNOS) inhibitors, is synthesized using diisopropyl (R)-(+)-malate as the starting material. The key steps involve a Frater-Seebach diastereoselective alkylation and a fast intramolecular cyclization. ...[more]

PMID: 19860389

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