Potassium Carbonate → (S)-a-Hydroxy-cyclopentanepropanoic acid

Reaction equation

C([O:4][C@@H:5]([CH2:9][CH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1)[C:6]([OH:8])=[O:7])(=O)C.C([O-])([O-])=O.[K+].[K+]>CO.O>[OH:4][C@@H:5]([CH2:9][CH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1)[C:6]([OH:8])=[O:7]

Participants

Procedure

A solution of 395 mg (1.97 mmol) of 2-(S)-acetoxy-3-(cyclopentyl)propanoic acid (from Step E) in 10 mL MeOH and 1 mL of H2O was treated with 1.29 g (9.33 mmol) of K2CO3 and stirred at rt for 30 h. The volatiles were removed under reduced pressure. The crude product was partitioned between 100 mL of ether and 100 mL of H2O and the layers were separated. The aqueous layer was acidified to pH 1-2 using 2.0 N HCl and extracted with 3×150 mL of EtOAc. The combined organic layers were dried over Na2SO4 and concentrated to give 287 mg (92%) of the title compound: 1H NMR (300 MHz) δ 1.11-2.15 (m, 11H), 4.27 (dd, J=8.1, 4.7, 1H), 6.5 (br, 1H).