Process for manufacturing simvastatin from lovastatin or mevinol

Details Process for manufacturing simvastatin from lovastatin or mevinol Process for manufacturing simvastatin from lovastatin or mevinol

1997-03-13

1998-06-09

Shippen, Michael L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

549292, C07C 6702

Patent

active

057636460

ABSTRACT:
A process for preparing simvastatin from lovastatin or mevinolinic acid in salt form comprises treating either starting material with cyclopropyl or butyl amine, the pyranone ring thereby being opened when lovastatin is the starting material, adding a methyl group to the 2-methylbutyrate side chain, and thereafter closing the open pyranone ring to produce simvastatin. The process is performed without protecting and deprotecting the two hydroxy groups of the open pyranone ring. In a preferred embodiment, the starting material is treated with cyclopropyl amine which produces simvastatin via the novel intermediate lovastatin cyclopropyl amide.

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"Synthesis of Synvinolin: Extremely High Conversion Alkylation of an Ester Enolat," D. Askin, T.R. Verhoeven, T. M.H. Liu, I. Shinkai, J. Org. Chem., 56, pp. 4929-4932 (1991).

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