Hydrochloric Acid → 5-Biphenyl-4-yl-3-hydroxy-pentanoic acid tert-butyl ester

Participants

Reaction Steps

Sodium borohydride (51 mg, 1.4 mmol) was added in one portion to a stirred solution of 5-biphenyl-4-yl-3-oxo-pentanoic acid tert-butyl ester (Intermediate 2, 400 mg, 1.23 mmol) in methanol (5 mL) at 0° C. under nitrogen. Stirring was continued for 30 mrrinutes then 1 M hydrochloric acid (5 mL) was added. The crude reaction mixture was extracted with diethyl ether (3×20 mL) and the resulting organic phases were combined, dried (MgSO4) then the solvent removed by evaporation under reduced pressure to give the title compound (375 mg, 93%) as a colourless oil. LC/MS: 3.67 min; z/e 344, calcd (M+NH4) 344.1H NMR (400 MHz: CDCl3): 7.55 (2 H), 7.50 (2 H), 7.43 (2 H), 7.38 (3 H), 4.01 (1 H), 3.25 (1 H), 2.80 (2 H), 2.44 (2 H), 1.82 (2 H), 1.45 (9 H).

Provenance & Evidence