Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | (Trifluoromethyl)trimethylsilane | HCID 552549 | — |
| Reactant | TBAF tetrahydrofuran | HCID 11078149 | — |
| Reactant | benzyl (2S)-2-methyl-3-oxopyrrolidine-1-carboxylate | HCID 59556933 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59273049 | HCID 59273049 | 81% |
Reaction Steps
To a solution (10 mL) of benzyl (2S)-2-methyl-3-oxopyrrolidine-1-carboxylate (1.0 g) in THF were added trifluoromethyltrimethylsilane (0.95 mL) and 1 mol/L tetrabutylammonium fluoride—THF solution (0.43 mL) under ice-cooling, and the mixture was stirred at room temperature for 18 hr. A 1 mol/L tetrabutylammonium fluoride—THF solution (8.56 mL) was added to the reaction mixture, and the mixture was stirred at 50° C. for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→2:1) to give the title compound as colorless oil (yield: 1.06 g, yield: 81%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08013008B2 |
|---|
| Source dataset | uspto-grants-2011_09 |
|---|
| ORD ID | ord-a8b3ab3d72b54ae587b2c20e08dfb699 |
|---|
| Source note | uspto-grants-2011_09 |
|---|