HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → (2R,4R)-2-[2-Fluoro-4-(2-oxo-piperidin-1-yl)-phenylcarbamoyl]-4-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline | HCID 27833 | — |
| Reactant | (2R,4R)-1-[(tert-butoxy)carbonyl]-4-methoxypyrrolidine-2-carboxylic acid | HCID 11459222 | — |
| Reactant | 1-(4-Amino-3-fluoro-phenyl)-piperidin-2-one | HCID 11789010 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (2R,4R)-2-[2-Fluoro-4-(2-oxo-piperidin-1-yl)-phenylcarbamoyl]-4-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester | HCID 11154790 | — |
Reaction Steps
Into a solution of 6 (0.250 g, 1.02 mmol) in CHCl3 (10 mL) was added 7 (0.212 g, 1.02 mmol), EEDQ (0.302 g, 1.22 mmol), and triethylamine (0.213 mL, 1.53 mmol). The solution was stirred at reflux for 19 h before cooling to RT and adding EtOAc. The solution was washed sequentially with 10% aq. citric acid, 1N NaOH, water, and brine, before drying over MgSO4 and concentrating under reduced pressure. The crude material was purified by flash chromatography to reveal 8 (0.329 g, 74%) as a tan foam. MS: APCI (AP+): 436.1 (M)+, (AP−): 434.1 (M)−.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07407972B2 |
| Source dataset | uspto-grants-2008_08 |
| ORD ID | ord-9e50e61e092249118156d3f73813791b |
| Source note | uspto-grants-2008_08 |