HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methoxytri-n-butylstannane → (8R,9S,13S,14S)-13-ethyl-3-methoxy-7,8,9,11,12,14-hexahydro-6H-cyclopenta[a]phenanthren-17-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methoxytri-n-butylstannane | HCID 11964040 | — |
| Reactant | (13S)-Ethyl-3-methoxygona-1,3,5(10),16-tetraen-17-ol Acetate | HCID 14257187 | — |
| Reactant | Allylmethyl carbonate | HCID 23349072 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | (8R,9S,13S,14S)-13-ethyl-3-methoxy-7,8,9,11,12,14-hexahydro-6H-cyclopenta[a]phenanthren-17-one | HCID 14257189 | — |
Reaction Steps
3.4 g of 17-acetoxy-3-methoxy-18-methyl-1,3,5(10),16-estratetraene is refluxed for 1.5 hours in 50 ml of acetonitrile with 2.3 ml of allylmethylcarbonate, 220 mg of palladium acetate and 580 microliters of tributyltin methoxide. The reaction mix is then diluted with water, extracted with dichloromethane and concentrated under vacuum. After chromatographic purification, 2.1 g of 3-methoxy-18-methyl-1,3,5(10),15-estratetraen-17-one with a melting point of 158°-160° C. is obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04923640 |
| Source dataset | uspto-grants-1990_05 |
| ORD ID | ord-95a999309b8c4483b9256bf1acf92cda |
| Source note | uspto-grants-1990_05 |