Resolution of D,L-dehydroproline

Details Resolution of D,L-dehydroproline Resolution of D,L-dehydroproline

1975-08-11

1978-01-03

Daus, Donald G.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2603264, 260DIG8, C07D20722

Patent

active

040666581

ABSTRACT:
D,L-3,4-dehydroproline is resolved in high optical yield by conversion to its N-protected derivative, treatment with R(+)alpha-methyl-p-nitrobenzylamine to form the diastereomeric salts, fractional crystallization, decomposition of the L-R salt and regeneration of the secondary amine group. The product L-3,4-dehydroproline obtained in extremely high optical purity is useful as an inhibitor of collagen synthesis.

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Robertson et al.; J. Am. Chem. Soc., vol. 84, pp. 1697-1701 (1962).

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