HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisobutylaluminumhydride → (3S)-3-(triethylsilyloxy)-3-(6-quinolyl)propanal
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisobutylaluminumhydride | HCID 21225700 | — |
| Reactant | (2R)-N-[3-(triethylsilyloxy)-3-(6-quinolyl)-propionyl]bomane-10,2-sultam | HCID 22901233 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | (3S)-3-(triethylsilyloxy)-3-(6-quinolyl)propanal | HCID 86586607 | — |
Reaction Conditions
| Temperature | -78 °C |
|---|
Reaction Steps
A solution of (2R)-N-[3-(triethylsilyloxy)-3-(6-quinolyl)-propionyl]bornane-10,2-sultam (52.8 gm) in 1000 mL of CH2Cl2 is cooled to −78° C, and a 1.0 M solution of diisobutylaluminum hydride in hexane is added dropwise so as to keep the reaction temperature below −65° C. The mixture is stirred for an additional 6 hours at −78° C., then is quenched by addition of sat. aq. NH4Cl and allowed to warm to ambient temperature. The mixture is washed with brine, and the organic phase is dried over MgSO4, filtered, and evaporated. The product is purified by silica gel chromatography.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06489314B1 |
| Source dataset | uspto-grants-2002_12 |
| ORD ID | ord-f017f5741a694401b80a15a5c10c266b |
| Source note | uspto-grants-2002_12 |