HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 4,4-Difluoro-pyrrolidine-1,2-dicarboxylic acid 2-[2-(6-bromo-naphthalen-2-yl)-2-oxo-ethyl]ester 1-tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Bromo-1-(6-bromonaphthalen-2-yl)ethanone | HCID 12698898 | — |
| Reactant | 1-((Tert-butoxy)carbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid | HCID 23512514 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 4,4-Difluoro-pyrrolidine-1,2-dicarboxylic acid 2-[2-(6-bromo-naphthalen-2-yl)-2-oxo-ethyl]ester 1-tert-butyl ester | HCID 66620864 | 83% |
Reaction Steps
2-Bromo-1-(6-bromo-naphthalen-2-yl)-ethanone (1 g, 3.07 mmol) and 4,4-Difluoro-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (849 mg, 3.38 mmol) were suspended in MeCN (15 mL) and treated with Et3N (0.45 mL, 3.22 mmol). After stirring o/n, the reaction mixture was concentrated. The resulting residue was dissolved in EtOAc and washed with water, saturated aqueous NaHCO3 and brine. The organic layer was dried over MgSO4, filtered and concentrated. The crude material was purified by silica column chromatography (0% to 20% EtOAc/Hex) to provide the title compound (1.27 g, 83%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08841278B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-47dc7af68cd54249a8c1be009e2f617e |
| Source note | uspto-grants-2014_09 |