HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 2-(4-Aminophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Tert-butyl 2-(4-nitrophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate | HCID 67085545 | — |
| Product | 2-(4-Aminophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole | HCID 58258856 | 25% |
Reaction Steps
The product of step A was subjected to Boc-deprotection with TFA following the procedure of Example 28, step B. The crude material was purified by flash column chromatography (SiO2, 1:9 methanol/dichloromethane) to give 2-(4-aminophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole (25 mg, 25%) as a yellow oil: 1H NMR (CDCl3, 300 MHz) δ 8.16 (s, 1H), 7.49-7.65 (m, 4H), 6.62-6.67 (m, 2H), 5.24-5.25 (m, 1H), 4.51-4.53 (m, 1H), 3.68 (s, 3H), 3.34-3.50 (m, 1H), 2.97-3.05 (m, 1H), 2.34-2.45 (m, 2H), 2.20-2.27 (m, 1H), 1.96-1.98 (m, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08575186B2 |
| Source dataset | uspto-grants-2013_11 |
| ORD ID | ord-917e94dd058042bcb51f743d1b2b1f28 |
| Source note | uspto-grants-2013_11 |