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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 13
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Original Articles

A New Way to tert-Butyl [(4R,6R)-6-Aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate, a Key Intermediate of Atorvastatin Synthesis

Pages 2275-2283 | Received 01 Oct 2002, Published online: 17 Aug 2006
 

Abstract

A new synthesis of tert-butyl [(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate, a key intermediate of the synthesis of an effective HMG-CoA reductase inhibitor atorvastatin, is described. The synthesis is based on the Henry reaction of nitromethane and tert-butyl [(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl] acetate. The formed nitroaldol was then O-acetylated and the sodium borohydride reduction of the intermediate provided tert-butyl [(4R,6R)-2,2-dimethyl-6-nitroethyl-1,3-dioxan-4-yl] acetate. Catalytic hydrogenation of the nitro group led to the title compound.

Acknowledgment

Financial support provided by Leciva Praha is greatly appreciated.

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