CYCLOHEXANE COMPOUNDS: II. SYNTHESIS AND STRUCTURE OF TWO STEREOISOMERIC 3-AMINO-1,2-CYCLOHEXANEDIOLS

Abstract

The stereoisomeric 1-ethoxy-2,3-epoxycyclohexanes were prepared from 1-ethoxycyclohexene-2 via 1-ethoxycyclohexene-2 bromohydrin. Ammonolysis of the lower- and higher-boiling oxides furnished 1α-ethoxy-2β-hydroxy-3α-aminocyclohexane and 1α -ethoxy-2β-hydroxy-3α-aminocyclohexane respectively. In a similar manner, 1α-methoxy-2α-hydroxy-3β-aminocyclohexane and lα-methoxy-2β-hydroxy-3α-aminocyclohexane were obtained from l-methoxycyclohexene-2 via 1-methoxycyclohexene-2 bromohydrin and the stereoisomeric 1-methoxy-2,3-epoxycyclohexanes. Ether cleavage of 1α-ethoxy- and lα-methoxy-2β-hydroxy-3α-aminocyclohexane gave 3α-amino-1α,2β-cyclohexanediol hydrobromide, from which the free base was obtained. 3β-Amino-1α,2α-cyclohexanediol was prepared similarly from lα-ethoxy- and 1α-methoxy-2α-hydroxy-3β-aminocyclohexane. The stereochemistry of the 3-amino-1,2-cyclohexanediols, 1-alkoxy-2-hydroxy-3-aminocyclohexanes, and 1-alkoxy-2,3-epoxycyclohexanes has been elaborated.