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 | — |
| Solvent | Methanol | HCID 887 | — |
| 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, methanol, 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 | US05001144 |
| Source dataset | uspto-grants-1991_03 |
| ORD ID | ord-93c6a2aef4ef4535bc5317afd7a33edb |
| Source note | uspto-grants-1991_03 |