Triethanolamine → (R)-1-(3-tert-butoxyphenyl)ethylamine

Participants

Reaction Steps

(R)—N-1-(3-tert-Butoxyphenyl)ethylmethoxyacetamide from example 2.3 (63.5 g with a purity of 93%; corresponds to 0.22 mol of pure substance) was mixed with triethanolamine (6 ml) with stirring and then admixed with 50% NaOH (23.2 g, 0.29 mol). The mixture was then stirred at a bath temperature of 140° C. for another 16 hours, after which all of the amide had reacted according to GC analysis. The mixture was diluted with water (100 ml), cooled and extracted with tert-butyl methyl ether (3×100 ml). The combined extracts were washed with saturated sodium chloride solution (50 ml) and dried over Na2SO4. After the solvent had been removed on a rotary evaporator, 41 g (92%) of (R)-1-(3-tert-butoxyphenyl)ethylamine were obtained in the form of a colorless oil. The chemical purity was 99.4%, the optical purity 98.9% ee.

Provenance & Evidence