New Route for the Synthesis of Chiral Hydrazine SADP

Tao      Jia

Abstract

A convenient route for the synthesis of (S)-1-amino-2-(1-methoxy-1-methylethyl)pyrrolidine (SADP) was established. The route involved three key steps viz. the Grignard addition to the N-Boc-proline ester (1), nitrosation to the aminoalcohol hydrochloride (3) and O-methylation to the alcohol group of N-nitrosopyrrolidine (4). (S)-1,1-dimethyl– tetrahydropyrrolo[1,2-c]oxazol-3-one (6) was also obtained via the reaction of (S)-1-Boc-2-(1-hydroxy-1- methylethyl)pyrrolidine (2) with sodium hydride.

Keywords: Chiral hydrazine, Grignard addition, nitrosation, O-methylation, SADP, hydride, pyrrolidine, carbonyl group, aldehyde, ester