Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Bromomethylcyclopropane | HCID 81503 | — |
| Reactant | 14-Hydroxymorphine-6-one | HCID 15286253 | — |
| Product | Naltrexone | HCID 5360515 | 88.6% |
Reaction Steps
Naltrexone can be produced from noroxymorphone by various direct and indirect alkylation methods. One method is by direct alkylation of noroxymorphone with cyclopropylmethylbromide. This process has been disclosed in general terms by Rice in WO 91/05768. Sanofi-Avensis (WO 2008/034973) describes a process for obtaining naltrexone in 88.6% yield by reacting noroxymorphone hydrochloride with cyclopropylmethylbromide in dimethylacetamide in the presence of sodium hydrogen carbonate. Cilag (WO 2008/138605) describes N-alkylation of noroxymorphone with cyclopropylmethylbromide in N-methyl-pyrrolidone in the presence of sodium hydrogen carbonate. Mallinckrodt (WO 2010/039209) describes N-alkylation of noroxymorphone with cyclopropylmethylbromide in the presence of a protic solvent. Specific examples in WO 2010/039209 describe the addition of water, isopropanol or ethanol as the protic solvent.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08580963B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-8a7572152f29450f905480eeb6671348 |
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| Source note | uspto-grants-2013_11 |
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