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. Alkalization with 2 M 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 ##STR30##

Provenance & Evidence