HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → Abiraterone Acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 3beta-Acetoxyandrost-5-en-17-one | HCID 14709 | — |
| Reactant | 3-(Diethylboryl)pyridine | HCID 642851 | — |
| Reactant | ((3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-(trifluoromethylsulfonyloxy)-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta(a)phenanthren-3-yl) acetate | HCID 10457059 | — |
| Reactant | Vinyl triflate | HCID 11769071 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Abiraterone Acetate | HCID 9821849 | — |
Reaction Steps
The crude vinyl triflate thus obtained (about a 4:1 mixture of vinyl triflate and prasterone acetate) is taken up with tetrahydrofuran (3.7 L). Diethyl(3-pyridyl)borane (90 g), bis(triphenylphosphine)palladium II chloride (3.8 g) and a 2M sodium carbonate aqueous solution (1 L) are loaded under inert gas environment. The resulting mixture is refluxed for about 1 h, then cooled to room temperature, and ethyl acetate (2.5 L) and water (2.5 L) are added. The aqueous phase is back-extracted with ethyl acetate (1.4 L), the combined organic phases are treated with decolourising carbon (about 100 g), and then concentrated under vacuum to obtain crude abiraterone acetate as an oil (320 g; purity about 87%; assay 51%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09340571B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-d7acb025435c4a3f91b314e9a17092be |
| Source note | uspto-grants-2016_05 |