Process for chiral 3-(1-amino-1,1-bisalkylmethyl)-1-substituted-

Details Process for chiral 3-(1-amino-1,1-bisalkylmethyl)-1-substituted- Process for chiral 3-(1-amino-1,1-bisalkylmethyl)-1-substituted-

1993-07-07

1994-09-13

Ramsuer, Robert W.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548542, 548557, C07D20750, C07D20709

Patent

active

053470176

ABSTRACT:
The process for the preparation of chiral 3-(1-amino-1,1-bisalkylmethyl)-1-substituted-pyrrolidines used as key intermediates for the preparation of naphthyridine and quinolone antibacterial agents which comprises reacting readily available chiral 1-substituted-3-pyrrolidinols to their corresponding chiral sulfonate esters; converting the sulfonate esters to chiral 1-substituted-3-cyanopyrrolidines having an inverse configuration, and then dialkylating the chiral cyanopyrrolidines with alkyl lithium in the presence of a Lewis acid without racemization at the asymmetric carbon atom is described.

REFERENCES:
patent: 5072001 (1991-12-01), Hagen et al.
patent: 5157128 (1992-10-01), Hagen et al.
Syn. Commun., 13, 1117 (1983) "Synthetic Routes to 3-Pyrrolidinol", Bowers, M. et al.
Ciganek, E. "Tertiary Carbinamines by Addition of Organocerium Reagents to Nitriles and Ketimines" J. Organic Chemistry, 57, pp. 4521-4527, 1992.

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