Reduction of an enaminone: Synthesis of the diamino alcohol core of ritonavir

…, L Bhagavatula, M Fitzgerald, SM Hannick…

Index: Haight, Anthony R.; Stuk, Timothy L.; Allen, Michael S.; Bhagavatula, Lakshmi; Fitzgerald, Michael; Hannick, Steven M.; Kerdesky, Francis A.J.; Menzia, Jerome A.; Parekh, Shyamal I.; Robbins, Timothy A.; Scarpetti, David; Tien, Jien-Heh J. Organic Process Research and Development, 1999 , vol. 3, # 2 p. 94 - 100

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Citation Number: 41

Abstract

The reduction of (5 S)-2-amino-5-dibenzylamino-4-oxo-1, 6-diphenylhex-2-ene was optimized for diastereoselectivity and overall conversion to (2 S, 3 S, 5 S)-5-amino-2- dibenzylamino-3-hydroxy-1, 6-diphenylhexane (2a). A two-step reduction sequence is described wherein the enamine is reduced with a borane-sulfonate derivative followed by reduction of the resulting ketone with sodium borohydride. The desired 2a was obtained ...