HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 4-[(2S,3R)-2-ethyl-3-hydroxy-5-oxopyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 4-[(2S,3R)-3-(tert-butyldimethylsilyloxy)-2-ethyl-5-oxopyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile | HCID 59556906 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-[(2S,3R)-2-ethyl-3-hydroxy-5-oxopyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile | HCID 59556874 | 53.2% |
Reaction Steps
To a solution of 4-[(2S,3R)-3-(tert-butyldimethylsilyloxy)-2-ethyl-5-oxopyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile (1.32 g) in tetrahydrofuran (30 mL)-ethanol (15 mL) was added 6 mol/L hydrochloric acid (15 ML), and the mixture was stirred at room temperature for 18 hr. Saturated aqueous sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane/ethyl acetate=6/1→1/9) to give the title compound as a colorless solid (yield: 507.3 mg, 53%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07834051B2 |
| Source dataset | uspto-grants-2010_11 |
| ORD ID | ord-9156af6121cc4f0b9e7be86df3ad0e4b |
| Source note | uspto-grants-2010_11 |