Chiral pyrrolidine core compounds en route to inhibitors of nitric oxide synthase
Diastereomeric pyrrolidine compounds and methods of preparation, as can be used en route to the preparation of a range of nitric oxide synthase inhibitors.
1. A compound of a formula
wherein R 1 is selected from C(O)OR′ 1 , CH 2 OH and CH 2 SO 3 CH 3 moieties, where R′ 1 is selected from the C 1 -about C 6 alkyl and C 1 -about C 6 substituted alkyl moieties; R 2 is selected from C 1 -about C 6 alkyl and C 1 -about C 6 substituted alkyl moieties; R 3 is selected from H and alkyl moieties; and R 4 is selected from H, amino and protected amino moieties, and a salt thereof.
2. The compound of claim 1 wherein R 3 is an alkyl moiety, and R 4 is a 2,5-dimethylpyrrol-1-yl moiety.
3. The compound of claim 1 selected from (2S,3R) and (2R,3S) diastereomers.
4. The compound of claim 1 wherein R 2 is a benzyl moiety.
5. The compound of claim 4 wherein R 1 is a CH 2 SO 3 CH 3 moiety, said compound mesylated to promote intramolecular cyclization.