HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 66687867, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Perfluoro-1-butanesulfonyl fluoride | HCID 67814 | — |
| Reactant | N,N-Diethylethanamine trihydrofluoride | HCID 175505 | — |
| Reactant | (R)-2-(3,4-dichloro-benzoyl)-4-hydroxy-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester | HCID 66687330 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 66687867 | HCID 66687867 | 99.5% |
Reaction Steps
To a stirred solution of (R)-2-(3,4-dichloro-benzoyl)-4-hydroxy-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.222 g, 0.554 mmol) in THF (3 mL) at ambient temperature under nitrogen was added perfluorobutanesulfonyl fluoride (0.195 mL, 1.11 mmol), triethylamine trihydrofluoride (0.181 mL, 1.11 mmol) and triethylamine (0.46 mL, 3.32 mmol). The reaction mixture was stirred for 18 hours, then filtered through a pad of silica, washed with EtOAc, and concentrated in vacuo to give (S)-2-(3,4-dichloro-benzoyl)-4-fluoro-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.222 g, 0.551 mmol, 99%) as a yellow foam that was used directly in the next step without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08513425B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-fb03d3d4f2ef444283ed300741969483 |
| Source note | uspto-grants-2013_08 |