Process for the preparation of substituted pyrrolidine...

Details Process for the preparation of substituted pyrrolidine... Process for the preparation of substituted pyrrolidine...

2007-06-12

2007-06-12

Saeed, Kamal A. (Department: 1626)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C548S556000

Reexamination Certificate

active

11210691

ABSTRACT:
Two syntheses are provided; one for the preparation of (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol, and other for the preparation of (3S,4R)-4-(hydroxymethyl)pyrrolidin-3-ol. (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol is prepared using the achiral ylide prepared from benzylamine instead of phenethylamine (Scheme 3) which provides a crystalline intermediate. The synthesis of (3S,4R)-4-(hydroxymethyl)pyrrolidin-3-ol is achieved from (S)-diethylmalate as described in Scheme 4. A process for preparing camphor sultam is also provided.

REFERENCES:
Karlsson, et al., Tetrahedron; Asymmetry 12 (2001) 1977-1982.
Tetrahedron Letters 41 (2000) 2949-2951.
Tetrahedron Asymmetry 10 (1999) 2605-2616.

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