Tetrahedron

Improved synthesis of (2S, 5S)-5-tert-butylproline

L Halab, L Bélec, WD Lubell

Index: Halab, Liliane; Belec, Laurent; Lubell, William D Tetrahedron, 2001 , vol. 57, # 30 p. 6439 - 6446

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Citation Number: 19

Abstract

(2S, 5S)-N-Boc-5-tert-butylproline (1) was synthesized by an improved procedure featuring the conversion of (2S)-1-tert-butyldimethylsiloxy-2-N-(PhF) amino-5-oxo-6, 6- dimethylheptane (16) into its corresponding imino alcohol followed by directed hydride delivery to reduce the imine functionality with a 95: 5 diastereoselectivity. Ketone 16 was obtained from methyl 2-N-(PhF) amino-5-oxo-6, 6-dimethylheptanoate (13), a previously ...