Synthetic approaches to (1 S,3 R)-3-aminomethyl-2,2,3-trimethylcyclopentylmethanol and (1 S,3 R)-3-amino-2,2,3-trimethylcyclopentylmethanol from (+)-camphoric acid

Abstract

The title aminomethyl ( 5) and amino ( 6) alcohols, which are of interest as intermediates in the synthesis of carbocyclic analogues of nucleosides, were prepared from (+)-camphoric acid via methyl (1 S,3 R)-3-carbamoyl-2,3,3-trimethylcyclopentane carboxylate ( 8). Direct reduction of 8 gave 5 in 26% yield. Amino alcohol 6 was prepared in 11–53% overall yields by several approaches, each involving oxidative degradation of 8 followed by a reduction step.