Synthesis, configuration, and evaluation of two conformationally restrained analogs of phencyclidine

BR De Costa, C George, TR Burke Jr…

Index: Costa, Brian R. de; George, Clifford; Burke, Terrence R.; Rafferty, Michael F.; Contreras, Patricia C.; et al. Journal of Medicinal Chemistry, 1988 ,  vol. 31,  # 8  p. 1571 - 1575

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Citation Number: 9

Abstract

Brown oxidation of cis-bicyclo [3. l. 0] hexan-3-ol afforded bicyclo [3. l. 0] hexan-3-one in 98% yield. Treatment of this ketone with either phenyllithium or phenylmagnesium bromide in ether at room temperature followed by solvolysis of the resulting alcohol in a mixture of trifluoroacetic acid, sodium azide, and chloroform gave a mixture of cis-and trans-3-azido-3- phenylbicyclo [3. l. 0] hexanes. LAH reduction of this crude mixture of azides afforded a 1: ...