HuagongsheHuagongshe Chemistry Print Report · For research reference only
m-Chloroperbenzoic acid → 17,17-(Ethylendioxy)-5alpha-hydroxyandrostane-3-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | m-Chloroperbenzoic acid | HCID 70297 | — |
| Reactant | 5-Androsten-3beta-ol-17-one ethyleneketal | HCID 11823779 | — |
| Reactant | HCID 14135097 | HCID 14135097 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Product | 17,17-(Ethylendioxy)-5alpha-hydroxyandrostane-3-one | HCID 69134027 | 55% |
Reaction Steps
Following the procedures described for the preparation of 5α-hydroxyandrostane-3,17-dione (II-ad, Prepn. 4), starting from 17,17-(ethylendioxy)-5-androsten-3β-ol after epoxidation with mCPBA, reduction with LAH, and oxidation with IBX, 17,17-(ethylendioxy)-5α-hydroxyandrostane-3-one was obtained in 55% yield. 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ4.29 (s, 1H), 3.78 (m, 4H), 2.69-1.10 (m, 21H), 1.07 (s, 3H), 0.76 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08609644B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-c98abe13784f4c11ab609b0899c969dc |
| Source note | uspto-grants-2013_12 |