Methanol → 4'-Methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylic acid

Participants

Reaction Steps

A mixture of ethyl 4′-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylate (3.94 g, 11.7 mmol), lithium hydroxide (0.65 g, 27.1 mmol), MeOH (250 mL), and water (40 mL) was stirred at rt for 20 hr. LC-MS indicated completion of the reaction. The solvent was removed in vacuo and the residue was treated with water and acidified with 1N aq. HCl to pH=2-3. The aqueous phase was extracted with EtOAc (3×100 mL). The combined organic layers were washed with water, brine, dried and concentrated to yield the product as a white solid. LC-MS: 310.4 [M+1]+; 1H NMR (400 MHz, DMSO-d6): 13.29 (s, 1H), 8.21 (t, 1H, J=1.6 Hz), 7.99 (t, 1H, J=1.6 Hz), 7.98 (t, 1H, J=1.5 Hz), 7.64 (d, 2H, J=8.2 Hz), 7.31 (d, 2H, J=7.9 Hz), 3.50 (t, 2H, J=6.7 Hz), 3.43 (t, 2H, J=6.5 Hz), 2.36 (s, 3H), 1.98-1.78 (m, 4H).

Provenance & Evidence