Process for the Synthesis of 3-spiropiperidino Indolenines

Non-Confidential description of the invention

The invention is related to the synthesis of 3-Spiropiperidino Indolenines, more particularly it relates to process for the synthesis of 3-spiropiperidino indolenines from activated aziridines. 3-Spiropiperidino indolenine is a privileged heterocyclic scaffold with exceptional pharmaceutical significance. It constitutes structural cores of several naturally-occurring alkaloids with valuable biological activities. 3-Spiropiperidino indolenine derivatives have been used as a calcitonin gene-related peptide (CGRP) receptor antagonist for headache therapy,1 and as 11β-hydroxysteroid dehydrogenase type-1 enzyme inhibitors that are useful in the treatment and prophylaxis of obesity and diabetes. We have invented a practical synthetic route to a wide range of 3-spiropiperidino indolenines possessing an exocyclic olefinic moiety at the 2-position of the piperidine ring via one-pot Lewis acid catalyzed SN2-type ring opening of activated aziridines with 2-substituted 1H-indoles followed by Pd-catalyzed spirocyclization with propargyl carbonates.

Inventors

Dr. Manas Ghorai (Chem), Dr. Chandan Kumar Shahi (Post Doc, SCDT), Mr. Sajan Pradhan (Student, Chem), Dr. Aditya Bhattacharyya (Post Doc, Chem)

IPA

201811022517

Date of Filing

15/06/2018

Status

Date Of Grant

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