HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 69672526, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- | HCID 85083 | — |
| Reactant | HCID 86708802 | HCID 86708802 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 69672526 | HCID 69672526 | 78% |
Reaction Steps
2-Bromo-1-(4-bromo-3-(difluoromethoxy)phenyl)ethanone (6.65 mmol) and Boc-proline (1.72 g, 7.98 mmol) were suspended in MeCN (13 mL) and triethylamine (1.00 mL, 7.32 mmol) was added. The reaction mixture was stirred at RT for 14 h, then diluted with EtOAc. The organic solution was washed with water saturated aqueous NaHCO3 and brine, then dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue was purified by silica column chromatography (19% to 40% EtOAc/Hex) to afford (S)-2-(2-(4-bromo-3-(difluoromethoxy)phenyl)-2-oxoethyl) 1-tert-butyl pyrrolidine-1,2-dicarboxylate (2.48 g, 78% over 4 steps).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09156823B2 |
| Source dataset | uspto-grants-2015_10 |
| ORD ID | ord-7d0024c4d69e4d81a7ef406a1f0198cc |
| Source note | uspto-grants-2015_10 |