HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 86635308, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-Phenylethanol, (R)- | HCID 637516 | — |
| Reactant | HCID 86635309 | HCID 86635309 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86635308 | HCID 86635308 | 76% |
Reaction Steps
Crude ethyl (±)-(3-chlorocarbonyl-1,2,3,4-tetrahydro-carbazol-9-yl)-acetate (5 mmol) is dissolved in dry CH2Cl2 and treated with (R)-1-phenyl-ethanol (0.55 g, 5.4 mmol), DIEA (1.94 g, 15 mmol) and DMAP (61 mg, 0.5 mmol). The resulting yellow solution is stirred at rt overnight, diluted with EtOAc and successively washed with 0.1 N HCl, saturated aqueous NaHCO3, H2O and brine. The organic layer is dried over Na2SO4, filtered and evaporated. The residue is purified by column chromatography on silica gel (hexane/EtOAc 5:1) to provide the subtitle compound as yellow oil (1.36 g) in 76% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08039474B2 |
| Source dataset | uspto-grants-2011_10 |
| ORD ID | ord-e693cb1992594e159f1ccd95a0f1df6f |
| Source note | uspto-grants-2011_10 |