HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylborane → Methyl (E)-7-{2-(4-fluoro-3-methylphenyl)-4-(pyrrolidin-1-yl)-6,6-dimethylcyclohex-1-en-1-yl}-3,5-dihydroxyhept-6-enoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylborane | HCID 7357 | — |
| Reactant | Methyl acetoacetate | HCID 7757 | — |
| Reactant | Lithium diisopropylamide | HCID 2724682 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | (E)-3-{2-(4-fluoro-3-methylphenyl)-4-(pyrrolidin-1-yl)-6,6-dimethylcyclohex-1-en-1-yl}propenal | HCID 15056967 | — |
| Product | 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 | — |
Reaction Steps
In a manner similar to Scheme I, 33 (2.27 g, 6.65 mmol) was treated with the LDA derived anion of methyl acetoacetate (7.98 mmol) followed by triethylborane, methynol, and NaBH4. Workup and purification by HPLC using 1% Et3N in EtOAc as eluent provided the oily product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04939143 |
| Source dataset | uspto-grants-1990_07 |
| ORD ID | ord-3d12181950ee4146a37578c784cfe6a6 |
| Source note | uspto-grants-1990_07 |