Water → 5-Hydroxy-5-propyl-2-(4-trifluoromethoxy-phenyl)-hexahydro-cyclopenta[c]pyrrol-1-one

Participants

Reaction Conditions

Reaction Steps

Propylmagnesium bromide (0.2 mL, 0.6 mmol, 3M) was added to a solution of 2-(4-trifluoromethoxy-phenyl)-hexahydro-cyclopenta[c]pyrrole-1,5-dione (0.1 g, 0.33 mmol) in THF (10 mL), and the mixture was stirred for 3 h at room temperature and overnight at 35° C. The solution was cooled, then poured into water (25 mL) and extracted with ether (3×20 mL), dried over Na2SO4. The solvent was removed and the residue was purified by prep-TLC (petroleum/ethyl acetate=1:1) to yield the title compound (25 mg, 21%). 1H NMR (300 MHz, CDCl3): δ 7.62-7.60 (m, 2H), 7.32-7.23 (m, 2H), 4.11 (t, 1H, J=9.5 Hz), 3.71-3.67 (m, 1H), 3.18 (t, 1H, J=9.5 Hz), 2.95 (d, 1H, J=9.6 Hz), 2.25-2.21 (m, 1H), 1.98-1.88 (m, 2H), 1.81-1.76 (m, 1H), 1.61-1.34 (m, 4H), 0.95 (t, 3H, J=7.2 Hz); LC-MS: 344.2 [M+1]+.

Provenance & Evidence