Triethanolamine → (R)-1-(4-tert-butoxyphenyl)ethylamine

(R)—N-1-(4-tert-Butoxyphenyl)ethylmethoxyacetamide from example 1.3 (180 g with a purity of 94%; corresponds to 0.64 mol of pure substance) was mixed with triethanolamine (20 ml) with stirring and then admixed with 50% NaOH (70.8 g, 0.89 mol). The mixture was then stirred at a bath temperature of 140° C. for another seven hours, after which all of the amide had been converted according to GC. 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, 123.7 g (73%) of (R)-1-(4-tert-butoxyphenyl)ethylamine were obtained in the form of a pale brownish oil. The chemical purity was 99.4%, the optical purity 98.9% ee.

1. stirringThe mixture was then stirred at a bath temperature of 140° C. for another seven hours
2. temperaturecooled
3. extractionextracted with tert-butyl methyl ether (3×100 ml)
4. washThe combined extracts were washed with saturated sodium chloride solution (50 ml)
5. dry with materialdried over Na2SO4
6. customAfter the solvent had been removed on a rotary evaporator

ORD record

ord-cc9fb6da51cc42da9da4b1c2073b15d1

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07968328B2