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

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Reaction Steps

Intermediate 5 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, 7.5:2.5 hexane/ethyl acetate) to give tert-butyl 2-(3-cyanophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (106 mg, 35%) as a yellow solid: 1H NMR (CDCl3, 300 MHz): δ 8.13-8.24 (m, 3H), 7.76 (td, J=7.8, 1.2 Hz, 1H), 7.66 (dd, J=8.7, 1.5 Hz, 1H), 7.60 (d, J=8.7 Hz, 1H), 7.34 (d, J=8.7 Hz, 1H), 5.20-5.37 (m, 1H), 4.58-4.82 (m, 1H), 3.62 (s, 3H), 3.25-3.50 (m, 1H), 2.52 (d, J=16.2 Hz, 1H), 2.13-2.42 (m, 2H), 1.88-2.00 (m, 1H), 1.55-1.68 (m, 1H), 1.38 (s, 9H).

Provenance & Evidence