Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | HCID 67085665 | HCID 67085665 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 67085675 | HCID 67085675 | — |
Reaction Steps
To a solution of the product of step B (100 mg, 0.06 mmol) in dichloromethane was added 2M HCl in diethylether (2 mL). After stirring at ambient temperature for 5 h the reaction mixture was concentrated in vacuo, triturated with ethyl acetate and lyophilized from water to give 2-phenylsulfonyl-5-isopropyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (50 mg, 57%, AUC HPLC >99%) as a white solid: mp 260-265° C., 1H NMR (CD3OD, 300 MHz) δ 8.26 (d, J=1.5 Hz, 1H), 7.93-7.97 (m, 2H), 7.67-7.76 (m, 2H), 7.51-7.59 (m, 3H), 5.28-5.30 (m, 1H), 4.69-4.75 (m, 1H), 4.52 (br s, 1H), 3.55 (dd, J=17.2, 5.1 Hz, 1H), 3.11 (d, J=17.4 Hz, 1H), 2.28-2.43 (m, 3H), 1.93-2.02 (m, 1H), 1.59 (d, J=7.2 Hz, 3H), 1.56 (d, J=6.9 Hz, 3H); ESI, m/z 381 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08575186B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-8280b978199e4bb48d926b9605aad4f3 |
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| Source note | uspto-grants-2013_11 |
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