Lithium Hydroxide → 5-(3-Benzyloxy-phenyl)-3-cyclopentyl-3-hydroxy-pentanoic acid

Participants

Reaction Steps

The title compound was prepared by dissolving (S) 5-(3-benzyloxy-phenyl)-3-cyclopentyl-3-hydroxy-pentanoic acid tert-butyl ester (1.6 g, 3.8 mmol) from Example CCCCC in methanol (20 mL). Lithium hydroxide (0.32 g, 7.6 mmol) in H2O (5 mL) was added and the reaction heated to reflux overnight, cooled and pumped to dryness under vacuum. The product was partitioned between H2O and Et2O. The aqueous layer was decanted, acidified with 1N HCl and extracted with EtOAc. The organic phase was dried (MgSO4), and concentrated to give the title compound. 1H-NMR (CDCl3) δ 1.3-1.7 (m, 8 H), 1.85-1.95 (m, 2 H), 2.3 (t, 1 H), 2.45-2.7 (m, 4 H), 5.1 (s, 2 H), 6.75-6.85 (m, 3 H), 7.15 (t, 1 H), 7.3-7.45 (m, 5 H).

Provenance & Evidence