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

Participants

Reaction Steps

Intermediate 1 was coupled with the product of Example 27, step B following the procedure of Example 27, step C. The crude material was purified by flash column chromatography (SiO2, 8:2 hexanes/ethyl acetate) to give tert-butyl 2-(3-chlorophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (110 mg, 35%) as an off-white solid: 1H NMR (CDCl3, 300 MHz) δ 8.17-8.23 (m, 1H), 7.92-7.96 (m, 1H), 7.83-7.88 (m, 1H), 7.65-7.73 (m, 1H), 7.46-7.50 (m, 1H), 7.41 (t, J=7.8 Hz, 1H), 7.34 (d, J=8.7 Hz, 1H), 5.20-5.36 (m, 1H), 4.60-4.73 (m, 1H), 3.63 (s, 3H), 3.30-3.50 (m, 1H), 2.52 (d, J=16.2 Hz, 1H), 2.15-2.42 (m, 2H), 1.90-2.01 (m, 1H), 1.58-1.60 (m, 1H), 1.39 (br s, 9H)

Provenance & Evidence