3-Aminotropane-3-carboxylic acids. Preparation and properties

Abstract

The two isomers of 3-aminotropane-3-carboxylic acid have been prepared by hydrolysis of the two α- and β-tropane-3-spiro-5′-hydantoins whose configurations were determined by X-ray crystallography and 13C nmr. The [Formula: see text] values of these amino acids and the hydrolysis rates of their N-formyl derivatives have been determined to study the influence of the amino group in an axial or equatorial position. The biological transport – inhibitory action of the two tropane amino acids has also been compared.

Complementary Ways to Diastereomers of Bridged Aminopiperidine Derivatives - A Stereochemical Challenge

“…The isomeric 3-endo-spirohydantoin 46a was formed directly from 36a, KCN and (NH 4 ) 2 CO 3 as the only reaction product [45,46]. Hydantoins 46a and 47a were hydrolyzed with sulfuric acid to give amino acids 48a and 49a in excellent yields, respectively [50]. Treatment of 45a with KCN and NH 4 Cl in the presence of CS 2 provided a 3-exospirodithiohydantoin [51].…”