Lithium hydroxide, monohydrate → (1R,3S)-3-(methoxycarbonyl)-2,2,3-trimethylcyclopentanecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

Lithium hydroxide hydrate (407 mg, 9.69 mmol) was added to a solution of (1S,3R)-dimethyl 1,2,2-trimethylcyclopentane-1,3-dicarboxylate (2.213 g, 9.69 mmol) in THF (27.7 ml), water (5.54 ml) and methanol (5.54 ml). The reaction was stirred at 55° C. for 14 hrs. The reaction was cooled to room temperature and concentrated under reduced pressure to yield an oil. The oil was diluted with ethyl acetate and washed with water. The aqueous layer was acidified with 1.0 N HCl, and was extracted with ethyl acetate (3×). The organic extracts were combined, dried with sodium sulfate, filtered and concentrated under reduced pressure, yielding the title compound (1.84 g, 8.59 mmol, 89% yield) as a colorless oil. LC/MS found [M+H]+=215.2. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 3.69 (3H, s), 2.84 (1 H, s), 2.52-2.65 (1 H, m), 2.13-2.24 (1 H, m), 1.81-1.90 (1 H, m), 1.53 (1 H, s), 1.27-1.32 (3 H, m), 1.22 (3 H, s), 0.84 (3 H, s).

Provenance & Evidence