Hydrochloric Acid → 5-Biphenyl-4-yl-3-hydroxy-2-methyl-pentanoic acid tert-butyl ester

Participants

Reaction Steps

Sodium borohydride (17 mg, 0.44 mmol) was added to a stirred solution of 5-biphenyl-4-yl-2-methyl-3-oxo-pentanoic acid tert-butyl ester (Intermediate 6, 135 mg, 0.399 mmol) in methanol (3 mL) at 0° C. under nitrogen. After stirring for 1 hour 1 M hydrochloric acid (5 mL) was added and the crude reaction mixture extracted with diethyl ether (3×5 mL). The organic phases were combined, washed with brine (5 mL) and dried (MgSO4). The volatiles were removed by evaporation under reduced pressure to give the title compound (130 mg, 96%) as a colourless gum, mixture of diastereoisomers. LC/MS: 3.72 min; z/e 341, calcd (M+1) 341.1H NMR (400 MHz: CDCl3): 7.59 (2 H), 7.51 (2 H), 7.42 (2 H), 7.28 (3 H), 4.21, 3.90, 3.65, 2.89, 2.75, 1.81, 1.69, 1.55, 1.44, 1.30, 1.18.

Provenance & Evidence