Synthesis of (Z)-and (E)-6-hydroxyketamine

…, A Trevor, T Baillie, N Castagnoli Jr

Index: Woolf, Thomas; Trevor, Anthony; Baillie, Thomas; Castagnoli, Neal Journal of Organic Chemistry, 1984 , vol. 49, # 18 p. 3305 - 3310

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Citation Number: 12

Abstract

2)-and (E)-6-hydroxyketamine, potential metabolites of the dissociative anesthetic agent ketamine [(A)-2-(o-chlorophenyl)-2-(methylamino) cyclohexanone], have been prepared by oxidation of the trimethylsilyl enol ether of N-(methoxycarbony1) ketamine with m- chloroperoxybenzoic acid. The relative stereochemistry of these diastereoisomers was established via the cyclic carbamate formed from the thermal cyclization of (E)-6-bromo-2- ...