Lithium Hydroxide → 2-(7-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)-9-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid

Participants

Reaction Conditions

Reaction Steps

Methyl 2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate (0.579 g, 1.192 mmol) was dissolved in 1,4-dioxane (10.74 mL). Aqueous 1.0 M lithium hydroxide (3.58 mL, 3.58 mmol) was added at 25° C. to give a slightly turbid solution. The reaction mixture was stirred at 60° C. for 1 h and cooled to 25° C. The solvent was evaporated in vacuo at 25° C. to a volume of 4 mL and added 0.5 M citric acid (14 mL) and MTBE (75 mL). The mixture was shaken. The organic layer was separated, washed with H2O (2×20 mL), brine (20 mL), and dried over MgSO4. The solvent was evaporated in vacuo to give the title compound (0.540 g) as white crystals. LCMS m/z=472.3 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.55-1.73 (m, 4H), 1.79-1.90 (m, 2H), 2.01 (m, 2H), 2.15 (s, 3H), 2.19-2.29 (m, 1H), 2.40-2.48 (m, 1H), 2.70-2.82 (m, 2H), 3.20-3.28 (m, 1H), 3.60 (m, 1H), 3.92 (m, 1H), 4.03 (m, 1H), 5.14 (s, 2H), 6.76 (dd, J=8.72, 2.40 Hz, 1H), 7.02 (d, J=2.40 Hz, 1H), 7.14 (d, J=8.72 Hz, 1H), 7.63 (d, J=8.00 Hz, 1H), 7.68-7.76 (m, 2H), 12.26 (bs, 1H).

Provenance & Evidence