HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → Trans-(E)-6-{2-{2-(4-fluoro-3-methylphenyl)-4-(pyrrolidin-1-yl)-6,6-dimethylcyclohex-1-en-1-yl}ethenyl}-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl chloroformate | HCID 10928 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Methyl (E)-7-{2-(4-fluoro-3-methylphenyl)-4-(pyrrolidin-1-yl)-6,6-dimethylcyclohex-1-en-1-yl}-3,5-dihydroxyhept-6-enoate | HCID 86744089 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Trans-(E)-6-{2-{2-(4-fluoro-3-methylphenyl)-4-(pyrrolidin-1-yl)-6,6-dimethylcyclohex-1-en-1-yl}ethenyl}-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one | HCID 86744090 | — |
Reaction Steps
In a manner similar to Scheme I, 34 (0.19 g) was treated with 2N NaOH in methanol at 0°-5° C. for 18 h, followed by ethyl chloroformate (0.254 mmol) and Et3N in CH2Cl2 at 0°-5° C. Workup and purification of the residue by SiO2 using 1% Et3N in EtOAc as eluent yielded the product. mp 120°-3° C. Anal. C26H34FNO3. 0.5 H2O: Theory C: 71.53; H: 8.08; N: 3.21; Found C.: 71.60; H: 8.17; N: 3.03.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05001144 |
| Source dataset | uspto-grants-1991_03 |
| ORD ID | ord-783ab6075147499ab4738472f6fab39f |
| Source note | uspto-grants-1991_03 |