Process for preparation of chiral 3-amino-pyrrolidine and analog

Details Process for preparation of chiral 3-amino-pyrrolidine and analog Process for preparation of chiral 3-amino-pyrrolidine and analog

1996-11-21

1997-12-30

McKane, Joseph

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D20709

Patent

active

057032440

ABSTRACT:
A process for the preparation of chiral 3-aminopyrrolidine and analogous bicyclic derivatives from dihydroxy olefins by treatment with titanium isopropoxide, an optically active tartrate ester and tert-butyl hydroperoxide, followed by subsequent alkylation of the intermediate with an alkyl or alkenyl magnesium halide, then pyrrolidine ring formation by condensation with an arylmethylamine, subsequent chiral replacement of a ring hydroxyl group with an amino group with further protection thereof, optional additional substitution closing of the second ring, and hydrogenolysis to remove a ring-nitrogen protecting group.

REFERENCES:
patent: 4990517 (1991-02-01), Petersen et al.
patent: 5059597 (1991-10-01), Petersen et al.
patent: 5140033 (1992-08-01), Schriewer et al.

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