Hydrochloric Acid → (1R,3S,4S)-3-methoxy-4-(nitrooxy)cyclopentanecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

A solution of methyl (1R,3S,4S)-3-methoxy-4-(nitrooxy)cyclopentanecarboxylate (0.66 g, 3.0 mmol) in methanol (12 mL) was cooled to 0° C. To this solution was added 4N potassium hydroxide (1.5 mL, 6.0 mmol) dropwise over 10 minutes, and the solution was stirred and allowed to warm to 10° C. over 3 hours. The reaction mixture was acidified by the addition of concentrated hydrochloric acid and extracted with chloroform (3×15 mL). The combined organic layers were washed with brine and dried (sodium sulfate) to give the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 2.06-2.14 (m, 2H), 2.34 (ddd, J=6.2, 9.1, 14.1 Hz, 1H), 2.54 (ddd, J=6.6, 8.7, 15.0 Hz, 1H), 3.03 (quintet, J=8.4 Hz, 1H), 3.38 (s, 3H), 3.82-3.86 (m, 1H), 5.27-5.32 (m, 1H), 8.5-11.5 (br, 1H).

Provenance & Evidence