Studies on Diastereofacial Selectivity of a Chiral tert-Butanesulfinimines for the Preparation of (S)-3-Methyl-1-(2-piperidin-1-yl-phenyl)butylamine for the Synthesis of Repaglinide

Periyandi Nagarajan; Chinnapillai Rajendiran; A. Naidu; P.K. Dubey

doi:10.14233/ajchem.2013.15539

Issue

Vol. 25 No. 16 (2013): Vol 25 Issue 16

Issue Published : October 9, 2013

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Studies on Diastereofacial Selectivity of a Chiral tert-Butanesulfinimines for the Preparation of (S)-3-Methyl-1-(2-piperidin-1-yl-phenyl)butylamine for the Synthesis of Repaglinide

https://doi.org/10.14233/ajchem.2013.15539

Periyandi Nagarajan

Suven Life Sciences Ltd., R & D Center, Plot No.18, Phase-III, IDA, Jeedimetla, Hyderabad-500 055, India ; Department of Chemistry, J.N.T. University, Hyderabad-500 085, India

Chinnapillai Rajendiran

Suven Life Sciences Ltd., R & D Center, Plot No.18, Phase-III, IDA, Jeedimetla, Hyderabad-500 055, India

A. Naidu

Department of Chemistry, J.N.T. University, Hyderabad-500 085, India

P.K. Dubey

Department of Chemistry, J.N.T. University, Hyderabad-500 085, India

Corresponding Author(s) : Periyandi Nagarajan

nagarajan@suven.com

Asian Journal of Chemistry, Vol. 25 No. 16 (2013): Vol 25 Issue 16
Article Published : October 9, 2013

Abstract

A new method for the asymmetric synthesis of a series of chiral amines including (S)-3-methyl-1-(2-piperidin-1-yl-phenyl)butylamine (2a) a key intermediate to prepare antidiabetic drug repaglinide by using Ellman’s reagent tert-butanesulfinamide. Diastereoselective addition of organometallic reagents to t-butanesulfinimines and followed by acidic and basic treatment. The obtained chiral amines were characterized by NMR, MS and other analytical data.

Keywords

S(-)-tert-butanesulfinamide 2-Piperdin-1-yl-benzaldehyde Titanium tetraethoxide R( )-tert-butanesulfinamide

Nagarajan, P., Rajendiran, C., Naidu, A., & Dubey, P. (2013). Studies on Diastereofacial Selectivity of a Chiral tert-Butanesulfinimines for the Preparation of (S)-3-Methyl-1-(2-piperidin-1-yl-phenyl)butylamine for the Synthesis of Repaglinide. Asian Journal of Chemistry, 25(16), 9345–9350. https://doi.org/10.14233/ajchem.2013.15539

Issue

Vol. 25 No. 16 (2013): Vol 25 Issue 16

Studies on Diastereofacial Selectivity of a Chiral tert-Butanesulfinimines for the Preparation of (S)-3-Methyl-1-(2-piperidin-1-yl-phenyl)butylamine for the Synthesis of Repaglinide

Corresponding Author(s) : Periyandi Nagarajan

Abstract

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