HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cyclohexylamine → (1R,4aR,7S)-1,4a,7-Trimethyl-7-vinyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-phenanthrene-1-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cyclohexylamine | HCID 7965 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | (1R,4aR,7S)-1,4a,7-Trimethyl-7-vinyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-phenanthrene-1-carboxylic acid | HCID 9861219 | — |
| Catalyst | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (1R,4aR,7S)-1,4a,7-Trimethyl-7-vinyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-phenanthrene-1-carboxylic acid | HCID 9861219 | — |
| Product | HCID 19097440 | HCID 19097440 | — |
Reaction Steps
Acanthoic acid, including compound obtained by the above described methodology, can be dissolved in dry CH2Cl2 and treated with 10 equivalents of (COCl)2 followed by two drops of DMF. When the reaction stops bubbling, the CH2Cl2 solvent and (COCl)2 can be evaporated under vacuum and the reaction residue can be redissolved in dry benzene and then treated with 5 equivalents of cyclohexylamine to yield N-cyclohexylamide derivative of acanthoic acid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08133915B2 |
| Source dataset | uspto-grants-2012_03 |
| ORD ID | ord-8c0339b93de64ef490700497f84031f5 |
| Source note | uspto-grants-2012_03 |