Sodium 2-methylbenzene-1-sulfinate → Tert-butyl 2-(2-methylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Participants

Reaction Steps

Intermediate 19 was coupled with the product of Example 27, step B following the procedure of Example 27, step C. The crude product was purified by flash column chromatography (SiO2, 8:2 hexanes/ethyl acetate) to give tert-butyl 2-(2-methylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (45 mg, 17%) as a light-yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.18 (dd, J=7.4, 1.5 Hz, 1H), 7.95 (dd, J=7.8, 1.8 Hz, 1H), 7.16-7.71 (m, 5H), 5.24 (br s, 1H), 4.70 (br s, 1H), 3.60 (s, 3H), 3.38 (br s, 1H), 2.50 (d, J=15.9 Hz, 1H), 2.49 (s, 3H), 2.26-2.47 (m, 1H), 2.13-2.26 (m, 1H), 1.88-1.99 (m, 1H), 1.59-1.67 (m, 1H), 1.37 (br s, 9H).

Provenance & Evidence