Methanol → (R)-5-(3-Hydroxypyrrolidine-1-carbonyl)-4'-methylbiphenyl-3-carboxylic acid

Participants

Reaction Steps

A mixture of (R)-ethyl 5-(3-hydroxypyrrolidine-1-carbonyl)-4′-methylbiphenyl-3-carboxylate (1.25 g, 3.54 mmol), lithium hydroxide (0.42 g, 18 mmol), methanol (50 mL), and water (5 mL) was stirred at rt for 4 h. LC-MS indicated completion of the reaction. The volatiles were removed in vacuo and the residue was treated with water and acidified with 1N aq. HCl to pH 2-3 and extracted with EtOAc (50 mL×3). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated to afford a white foam. LC-MS: 326.3 [M+1]+; 1H NMR (400 MHz, CD3OD): 8.33 (m, 1H), 8.11 and 8.10 (t, 1H, J=1.6 Hz), 7.98 and 7.97 (t, 1H, J=1.6 Hz), 7.57 (d, 2H, J=7.6 Hz), 7.30 (d, 2H, J=8.0 Hz), 4.51 and 4.38 (m, 1H), 3.85-3.35 (m, 4H), 2.39 (s, 3H), 2.20-1.90 (m, 2H).

Provenance & Evidence