Hydrochloric Acid → (2R)-2-amino-3-(3-thienyl)-1-propanol hydrochloride

Participants

Reaction Conditions

Reaction Steps

A solution of 1.4 g of N-[(1R)-2-hydroxy-1-(3-thienylmethyl)ethyl]acetamide in 17.6 cm3 of aqueous 6N hydrochloric acid is heated with stirring at a temperature in the region of 100° C. for 2 hours. The reaction mixture is then concentrated under reduced pressure (2 kPa) at a temperature in the region of 40° C. to give a greenish oil, which crystallizes from 60 cm3 of acetone. The crystals are filtered off on a sinter funnel, washed with acetone and then dried in an oven under vacuum (10 Pa) at a temperature in the region of 50° C. 0.92 g of (2R)-2-amino-3-(3-thienyl)-1-propanol hydrochloride is obtained in the form of an off-white solid. 1H NMR spectrum (400 MHz, (CD3)2SO-d6, δ in ppm): 2.93 (mt: 2H); from 3.25 to 3.50 (mt: 2H); 3.53 (broad d, J=11 Hz: 1H); 5.37 (unres. mult.: 1H); 7.07 (broad d, J=5 Hz: 1H); 7.35 (mt: 1H); 7.53 (dd, J=5 and 3 Hz: 1H); 8.18 (unres. mult.: 3H)

Provenance & Evidence