Process for synthesis of chiral cis- and trans-3-amino-4-substit

Details Process for synthesis of chiral cis- and trans-3-amino-4-substit Process for synthesis of chiral cis- and trans-3-amino-4-substit

1996-07-12

1997-04-08

McKane, Joseph

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D20709

Patent

active

056189494

ABSTRACT:
Process for preparation of chiral cis-3,4-substituted pyrrolidine compounds having the formulas ##STR1## and chiral 3,4-trans-substituted pyrrolidine compounds having the formulas ##STR2## with the assistance of a stereochemically directing chiral oxazolidinone moiety having the formula ##STR3## wherein P, R and R.sup.1 are specifically defined, by sequential reaction of the compound or subsequent intermediates with an a,b-unsaturated acid chloride, reaction with N-benzyl-N-(methoxymethyl)trimethylsilylmethylamine and separating isomers by chromatography, hydrolytic removal of the oxazolidinone moiety, reaction with diphenylphosphoryl azide and triethylamine, and debenzylating; and novel intermediates of the process.

REFERENCES:
CA 123: 313930s Preparation of . . . antibacterials. Chu et al. Apr. 1995.

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