HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethanol → trans-4-Hydroxy-5-phenyl-2,3,4,5-tetrahydo spiro(benzothiepine-3,1'-cyclohexane)-1,1-dioxide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | 8b-Phenyl-1a,2,3,8b-tetrahydrospiro(benzothiepino[4,5-b]oxirene-2,1'-cyclohexane)-4,4-dioxide | HCID 22325212 | — |
| Reactant | HCID 178418361 | HCID 178418361 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | trans-4-Hydroxy-5-phenyl-2,3,4,5-tetrahydo spiro(benzothiepine-3,1'-cyclohexane)-1,1-dioxide | HCID 59890377 | 40.1% |
Reaction Steps
A mixture of 0.5 g (1.4 mmoles) of 58 , 20 ml of ethanol,10 ml of methylene chloride and 0.4 g of 10% Pd/C catalyst was hydrogenated with 70 psi hydrogen for 3 h at room temperature. The crude reaction slurry was filtered through Celite and evaporated to dryness. The residue was purified by HPLC (10% EtOAc-Hexane, 25% EtOAc-Hexane). The first fraction was 300 mg (60%) as a white solid, mp 99-100° C. Proton NMR showed this was a trans isomer. The second fraction gave 200 mg of solid which was impure cis isomer.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06262277B1 |
| Source dataset | uspto-grants-2001_07 |
| ORD ID | ord-47d781fce34342099237f7172641e534 |
| Source note | uspto-grants-2001_07 |