HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → Rac-n-((3s,4r)-1-benzyl-4-phenyl-pyrrolidin-3-yl)-2-(3,5-bis-trifluoromethyl-phenyl)-n-methyl-isobutyramide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoyl chloride | HCID 11267141 | — |
| Reactant | rel-(3S,4R)-1-Benzyl-N-methyl-4-phenylpyrrolidin-3-amine | HCID 59840122 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Rac-n-((3s,4r)-1-benzyl-4-phenyl-pyrrolidin-3-yl)-2-(3,5-bis-trifluoromethyl-phenyl)-n-methyl-isobutyramide | HCID 87211937 | 74% |
Reaction Steps
A solution of 2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride (the preparation of which is described in WO2002079134) (0.88 g, 2.76 mmol) in CH2Cl2 (2 ml) was added drop wise to a stirred solution of rac-((3S,4R)-1-benzyl-4-phenyl-pyrrolidin-3-yl)-methyl-amine (0.72 g, 2.70 mmol) and ethyl-diisopropyl-amine (0.64 ml, 3.76 mmol) in CH2Cl2 (5 ml). The reaction mixture was stirred 1 h, concentrated under vacuo and purification by flash chromatography (SiO2, EtOAc/H, 1:4) yielded 1.05 g (74%) of the title product as colorless foam.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07893062B2 |
| Source dataset | uspto-grants-2011_02 |
| ORD ID | ord-2887b0bc2e884b99a5f1aa2cd5adfa71 |
| Source note | uspto-grants-2011_02 |