Process for preparing (trans)-4-phenyl-L-proline derivatives

Details Process for preparing (trans)-4-phenyl-L-proline derivatives Process for preparing (trans)-4-phenyl-L-proline derivatives

1988-06-17

1990-03-27

Brust, Joseph Paul

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548532, C07D20712

Patent

active

049122312

ABSTRACT:
A process is provided for preparing (trans)-4-phenyl-L-proline derivatives with excellent stereospecificity, which are useful in preparing certain ACE inhibitors, which process involves reacting a proline derivative of the structure ##STR1## whereing R is a nitrogen protecting group, R.sub.1 is H, aryl, arylalkyl or lower alkyl, and X is a leaving group such as fluorine, an alkyl sulfonate, arylsulfonate or cycloalkyl sulfonate is reacted with an aromatic nucleophile, such as benzene, in the presence of a Lewis acid such as AlCl.sub.3 to form the (trans)-4-phenyl-L-proline derivative of the structure ##STR2##

REFERENCES:
patent: 4501901 (1985-02-01), Thottathil et al.
patent: 4588819 (1986-05-01), Thottathil
Nakajima et al., Tetrahedron, vol. 25, pp. 1807-1816, 1969, "Stereospecific Alkylation of Benzene with (+)-Propylene Oxide by Lewis Acid Catalyst and Stereochemistry of Ring-Opening.sup.1,2 ".
Bauman et al., Journal of the American Chemical Society, 89:21, Oct. 11, 1967, pp. 5421-5424, "A Stereospecific Friedel-Crafts Reaction, The Alkylation of Benzene with .gamma.-Valerolactone".
Green et al., J. Org. Chem. 1985, 50, 3945-3946, "Alkylation of Aromatic Compounds with Optically Active Lactic Acid Derivatives: Synthesis of Optically Pure 2-Arylpropionic Acid and Esters".
Nakajima et al., Bulletin of the Chemical Society of Japan, vol. 52 (8), 2377-2382 (1979), "Alkylation of Benzene with Optically Active 3-Chloro-1-butanol, 3-Chlorobutanoic Acid, and Their Esters".
Suga et al., Bull, Chem. Soc. Jpn., 54, 3611-3612 (1981), "Stereochemistry of Friedel-Crafts Alkylation of Benzene with Optically Active 2-Chlorobutane".
Streitwieser et al., J. Amer. Chem. Soc., 1965, 87, p. 4953, "Boron Fluoride-Alcohol Alkylations, III, Stereochemistry of Alkylation of Benzene with 2-Propanol-1-d.sub.3.sup.1 ".
Hart, Friedel-Crafts and Related Reactions, ed. by G. A. Olah, vol. 1, pp. 999-1015, "Stereochemical Aspects".
Noller, Chemistry of Organic Compounds, 3rd Edition, 1965, p. 470.

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