Intermediates in the preparation of chiral hydantoins

Details Intermediates in the preparation of chiral hydantoins Intermediates in the preparation of chiral hydantoins

1981-11-12

1982-09-07

Schwartz, Richard A.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D491107

Patent

active

043485260

ABSTRACT:
A novel process for the synthesis of chiral hydantoins of the structure ##STR1## wherein X is fluoro or chloro, from the corresponding 6-halo-4-chromanone of the structure ##STR2## is described. The compounds I are valuable in the treatment of certain chronic complications arising from diabetes mellitus. In addition the compound of the formula I wherein X is chloro possesses complementary hypoglycemic activity.
The process comprises the sequence of dehydrative coupling of the halochromanone (II) with S-(-)-alpha-methylbenzylamine to form the imine of structure ##STR3## addition of hydrogen cyanide to form the nitrile of structure ##STR4## condensation with chlorosulfonylisocyanate (or its equivalent) to form the alpha-methylbenzylhydantoin of structure ##STR5## and finally solvolysis of the latter to the chiral hydantoin of structure I.

REFERENCES:
patent: 4117230 (1978-09-01), Sarges

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