Tetrahedron

Resolution of 4-Cyano-4-(4-nitrophenyl) hexanoic Acid: Synthesis of (R) and (S)-3-(4-Aminophenyl)-3-ethylpiperidine-2, 6-dione (Aminoglutethimide 1)

O Achmatowicz, I Malinowska, B Szechner, JK Maurin

Index: Achmatowicz, Osman; Malinowska, Iwona; Szechner, Barbara; Maurin, Jan K. Tetrahedron, 1997 , vol. 53, # 23 p. 7917 - 7928

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Citation Number: 12

Abstract

Using (R)-or (S)-1-phenylethylamine as a resolving agent,(R)-and (S)-4-cyano-4-(4- nitrophenyl) hexanoic acids have been isolated. Cyclization of each enantiomer, followed by reduction of the nitro group, afforded (R)-and (S)-aminoglutethimide of high (> 99% ee) enantiomeric purity, respectively. The absolute configuration of (R)-(+)-3-(4-nitrophenyl)-3- ethylpiperidine-2, 6-dione was solved by X-ray single crystal analysis thus establishing ...