Process for the preparation of the (-)-antipode of (E)-1-cyclohe

Details Process for the preparation of the (-)-antipode of (E)-1-cyclohe Process for the preparation of the (-)-antipode of (E)-1-cyclohe

1988-10-31

1990-08-21

Brust, Joseph Paul

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D20712

Patent

active

049507672

ABSTRACT:
A process for the preparation of an optically active proline derivative of the formula ##STR1## in which R.sup.1 is alkyl, phenyl or benzyl, or an acid addition salt thereof, comprising reacting an S-proline ester of the formula ##STR2## in which R.sup.2 is alkyl with 1 to 4 carbon atoms, in a first stage with benzyl chloroformate of the formula ##STR3## in the presence of an acid-binding agent and in the presence of a diluent, thereby to produce an ester with the S-configuration on the asymmetrically substituted carbon atom, of the formula ##STR4## reacting such ester in a second stage with a Grignard compound of the formula

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Enders et al., "Nucleophilic Alpha-Sec-Aminoalkylation . . . ", Organic Syntheses, B. 58, Dec. 1978, pp. 113-122.
90642w: Likhosherstov et al., "Aza Cycloalkanes.", Chem. Abstr. V. 67, No. 19, Nov. 1967, p. 8527.

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