Process for producing cyclohexylbutyric acid derivative

Details Process for producing cyclohexylbutyric acid derivative Process for producing cyclohexylbutyric acid derivative

1993-12-30

1995-08-15

Shippen, Michael L.

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

Organic compounds

Carboxylic acids and salts thereof

548239, 549549, 552 4, 552 10, 556418, 560125, 562 39, C07C 6108

Patent

active

054421055

ABSTRACT:
A process for for producing a (2R,3S)-cyclohexylnorstatine or a salt thereof is disclosed, which comprises the steps of: enantioselectively hydrogenating a 4-cyclohexyl-2-halogeno-3-oxobutyric acid ester in the presence of a ruthenium-phosphine complex to produce a 4-cyclohexyl-2-halogeno-(3R)-hydroxybutyric acid ester (2); epoxidizing the compound (2) in the presence of a base to produce a 4-cyclohexyl-(2S,3R)-epoxybutyric acid ester (3); reacting the compound (3) with a lower trialkylsilyl azide in the presence of a Lewis acid to produce a (3S)-azide-4-cyclohexyl-(2S)-substituted butyric acid ester (4); subjecting the compound (4) to hydrogenolysis to produce a (2S,3S)-cyclohexylnorstatine derivative (5); and inverting the configuration at the 2-position of the compound (5).

REFERENCES:
patent: 2446192 (1946-01-01), Pfister et al.
patent: 4711958 (1987-12-01), Iizuka et al.
patent: 4814342 (1989-03-01), Hoover et al.
patent: 4933482 (1990-06-01), Sayo et al.
English-language Abstract of JP-A-2-121963.
English-language Abstract of JP-A-1-172365.
J. Chem. Soc., Chem. Commun., 1989, p. 1678.
Chem. Lett., 1990, p. 723.
J. Med. Chem., 1990 33, p. 2707.

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