STEROIDS. I. A CASE OF WALDEN INVERSION WITH NUCLEOPHILIC SUBSTITUTION AT POSITION 3 OF Δ5–STEROIDS

Abstract

When 3(β)-chlorocholest-5-ene is heated with benzylamine, inversion with partial racemization occurs to give a mixture of N-benzyl-3(α)-aminocholest-5-ene and N-benzyl-3(β)-aminocholest-5-ene. The configurations of the N-benzyland N-acetyl-3-aminocholest-5-enes have been determined.The preparation of N,N-bis.-(2-chloroethyl)-3(ξ)-aminocholest-5-ene hydrochloride is described.