Development of a Scalable Synthesis of (S)-3-Fluoromethyl-γ-butyrolactone, Building Block for Carmegliptin's Lactam Moiety

JM Adam, J Foricher, S Hanlon, B Lohri…

Index: Adam, Jean-Michel; Foricher, Joseph; Hanlon, Steven; Lohri, Bruno; Moine, Gerard; Schmid, Rudolf; Wirz, Beat; Zutter, Ulrich; Stahr, Helmut; Weber, Martin Organic Process Research and Development, 2011 , vol. 15, # 3 p. 515 - 526

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Citation Number: 13

Abstract

Several new routes are reported for the synthesis of (S)-3-fluoromethyl-γ-butyrolactone. An asymmetric hydrogenation-based synthesis was chosen as the enabling route to produce the lactone on a 10-kg scale. A superior stereoselective route starting from (S)-tert-butyl glycidyl ether which afforded the desired lactone in three steps with∼ 50% overall yield was finally selected for further development and production.

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