Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Cyclopropanecarbonyl chloride | HCID 77637 | — |
| Reactant | HCID 58123690 | HCID 58123690 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 58123695 | HCID 58123695 | — |
Reaction Steps
Cyclopropylcarbonyl chloride (0.13 mL) is added to a solution of 1-[(2R,6S)-8-amino-9-hydroxy-6,11,11-trimethyl-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocin-3-yl]-2,2,2-trifluoro-ethanone (0.50 g) and triethylamine (0.25 mL) in dichloromethane (3 mL). After stirring the solution at room temperature overnight, concentrated aqueous ammonia solution (1 mL) and methanol (2 mL) are added and the resulting mixture is stirred for additional 2 h. Then, the solution is concentrated and water is added to the residue. The resulting mixture is extracted with ethyl acetate and the combined organic extracts are washed with brine and dried (MgSO4). The solvent is removed under reduced pressure to give the crude title compound that is used without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08859580B2 |
|---|
| Source dataset | uspto-grants-2014_10 |
|---|
| ORD ID | ord-10fbf455d57940aa91393a16c93cbaa3 |
|---|
| Source note | uspto-grants-2014_10 |
|---|