Water → HCID 12914029, compound

Participants

Reaction Steps

To 1.0 g (3.1 mmole) of 3-(4-bromophenyl)-3-hydroxy-3-(3-pyridyl)-propionamide and 0.8 g (0.02 mole) of sodium borohydride in 60 ml of dry tetrahydrofuran at 0° C. and under N2, was added dropwise over 20 minutes 4.6 g (0.03 mole) of boron trifluoride ethyl etherate in 20 ml of dry tetrahydrofuran. The mixture was stirred for 48 hours at room temperature, and then cautiously hydrolyzed with water. Alcalization with 2M NaOH and extraction with ether gave after evaporation a semi-crystalline residue. Recrystallization from ether-petroleum ether gave 0.6 g (63%) of the amine, m.p. 95°-115° C. NMR-spectrum (COCl3): 2H(2.4, 1-CH2)m : 2H(3.0, 2-CH2)m : 3H(3.6, --OH, --NH2)b : 6H(7.1-8.0 ArH)m : 2H(8.6)m ##STR31##

Provenance & Evidence