CYCLOPROPYL ALKYL AMINES AND PROCESS FOR THEIR PREPARATION

Abstract

The present invention relates to a process of making a compound of formula (I). Wherein, R is as defined herein.

##STR00001##

Claims

1. A compound having the following formula I: ##STR00007## wherein R is a C.sub.1-3 alkyl.

2. A process for making a compound of the formula I in claim 1, comprising reacting an amine of formula II with a suitable base and mandelic acid, in a suitable solvent, to provide a compound of formula I: ##STR00008## wherein R in formula I and II, is a C.sub.1-3 alkyl.

Description

SYNTHETIC EXAMPLE

Example 1

Synthesis of (S)-1-Cyclopropylethan-1-amine (R)-(-)-mandelate

[0019] ##STR00006##

[0020] A solution of (S)-1-cyclopropylethan- 1-amine hydrochloride in ethanol (EtOH, 15 V) is treated with 1.0 eq of 25 wt % aqueous sodium hydroxide (NaOH) at 20-25 C. After 1 h at 20-25 C., the resulting slurry is filtered through Celite to remove sodium chloride (NaCl). To (R)-(-)-mandelic acid is added a solution of (S)-1-cyclopropylethan-1-amine hydrochloride) in ethanol, obtained above. EtOH/water is removed by azeotropic distillation to 4 V, after which methyl tert-butyl ether (MTBE, 12 V) is added at 60 C. After controlled cooling, the batch is filtered, and the wetcake is washed with 1:3 EtOH/MTBE. The product is obtained as a white solid in 83-87% isolated yield with a GC purity of >99 A %, >95.sup.1H NMR wt %, and 99.5:0.5 er by GC analysis of the corresponding trifluoroacetamide derivative.