HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → 14-Hydroxydihydrocodeine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Ethanol | HCID 702 | — |
| Reactant | (4R,4aS,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one | HCID 5359420 | — |
| Reactant | HCID 178418361 | HCID 178418361 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Water | HCID 962 | — |
| Product | 14-Hydroxydihydrocodeine | HCID 5360241 | 84% |
Reaction Steps
14-Hydroxycodeinone (4.5 g) was warmed with ethanol (2.17 g/g 14-hydroxycodeinone) to 60-65° C. and acetic acid was added in portions until all solid dissolved. Following the addition of 10% Pd/C (dry, 0.01 g/g 14-hydroxycodeinone) and water (0.01 g/g 14-hydroxycodeinone) to compensate for the water in the dry Pd/C catalyst, the hydrogenation was performed with hydrogen being introduced at 80° C. The reaction was sampled after 22 h and was determined to be complete. This reaction resulted in low levels of 6α-oxycodol. After isolation (84% yield by LOD), the level of 6α-oxycodol was also determined to be low by analysis.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08916707B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-7a925e4519d342a7a53e9765dd023172 |
| Source note | uspto-grants-2014_12 |