Sodium 3-chlorobenzene-1-sulfinate → Tert-butyl 2-(3-chlorophenyl)sulfonyl-4,5-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

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Reaction Steps

Intermediate 1 was coupled to the product of Example 71, step C following the procedure of Example 71, step D. The crude product was purified by flash column chromatography (SiO2, 8:2 hexanes/ethyl acetate) to give tert-butyl 2-(3-chlorophenyl)sulfonyl-4,5-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (136 mg, 39%) as a light-yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.02 (s, 1H), 7.92 (t, J=1.8 Hz, 1H), 7.83 (dt, J=7.5, 1.5 Hz, 1H), 7.43-7.49 (m, 1H), 7.41 (d, J=7.8 Hz, 1H), 7.33 (s, 1H), 5.22 (br s, 1H), 4.71 (br s, 1H), 3.85 (s, 3H), 3.35 (br s, 1H), 2.76 (s, 3H), 2.45 (d, J=15.9 Hz, 1H), 2.12-2.38 (m, 2H), 1.86-1.97 (m, 1H), 1.52-1.66 (m, 1H), 1.37 (br s, 9H).

Provenance & Evidence