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

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Reaction Conditions

Reaction Steps

A solution of (+)-methyl (1R,3S,4S)-3-methoxy-4-(nitrooxy)cyclopentanecarboxylate (0.658 g, 3 mmol) in methanol (12 ml) was cooled to 0° C. To this was added 4N KOH (1.500 ml, 6.00 mmol) dropwise over 10 minutes and the solution was stirred and allowed to warm to 10° C. over 3 h. The reaction mixture was neutralized to pH 7 by addition of 0.5 mL concentrated HCl and then the solution was concentrated under vacuum to remove methanol. To the residue was added 10 ml CHCl3 and 2 mL water and the pH was adjusted to 3-4 by addition of 2M HCl. The layers were separated and the aqueous layer was washed with two 15 mL portions of CHCl3. The combined organic layers were washed with brine and dryed over Na2SO4 to give the title compound (0.566 g, 2.76 mmol, 92% yield) as a colorless oil; 1H NMR (500 MHz, CDCl3) δ 2.08-2.18 (m, 2H), 2.32-2.4 (m, 1H), 2.52-2.58 (m, 1H), 3.05 (quintet, J=8.3 Hz, 1H), 3.40 (d, J=0.7 Hz, 3H), 5.31 (m, 2H).

Provenance & Evidence