Tetrahydrofuran → methyl 2-(4-cyano-3-hydroxyphenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylate

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A mixture of 2-(3-(benzyloxy)-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid (Example 31; 70 mg, 0.14 mmol), ethyl acetate, tetrahydrofuran, and methanol was treated with 10% palladium on carbon (10 mg) and hydrogenated for four hours at 30 psi hydrogen. The mixture was filtered through Celite, and concentrated to give methyl 2-(4-cyano-3-hydroxyphenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylate (57 mg, 0.14 mmol) as a yellow solid. The title compound was largely present as (±)-(3RS,3aSR)-methyl 2-(4-cyano-3-hydroxyphenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylate. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.10-1.58 (m, 8H), 1.61-1.75 (m, 1H), 1.74-1.90 (m, 1H), 2.00-2.12 (m, 1H), 2.16-2.30 (m, 1H), 2.79-2.96 (m, 1H), 3.09 (d, J=16.11 Hz, 1H), 3.57 (ddd, J=13.76, 9.47, 4.70 Hz, 1H), 4.76 (dd, J=9.67, 5.37 Hz, 1H), 6.69 (dd, J=8.86, 1.61 Hz, 1H), 6.82 (s, 1H), 7.36 (d, J=8.59 Hz, 1H), 7.82-7.90 (m, 2H), 8.00 (d, J=8.06 Hz, 1H), 10.70 (s, 1H). ES-MS m/z 402 (M+H).

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