HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 3-(4-Fluorophenyl)-1-{[5-(4-methylphenyl)isoxazol-4-yl]carbonyl}pyrrolidin-3-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 3-(4-Fluorophenyl)pyrrolidin-3-ol hydrochloride | HCID 200556 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | 5-(p-Tolyl)isoxazole-4-carboxylic acid | HCID 22831706 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-(4-Fluorophenyl)-1-{[5-(4-methylphenyl)isoxazol-4-yl]carbonyl}pyrrolidin-3-ol | HCID 59170158 | 81.9% |
Reaction Steps
A solution of 5-(4-methylphenyl)isoxazole-4-carboxylic acid (20 mg, 0.1 mmol), TBTU (39 mg, 0.12 mmol, 1,2 equ.) and N-ethyl-N-isopropylpropan-2-amine (35 μL, 0.2 mmol, 2 equ) in DMF (1 mL) was added to 3-(4-fluorophenyl)pyrrolidin-3-ol hydrochloride (22 mg, 0.1 mmol) and the reaction mixture was left at rt for 2 h. The solvent was evaporated and the crude product was purified by RP-HPLC. After evaporation of the solvents the product was dried in vacuum to yield the title compound (30 mg). MS (ESI, pos. ion) m/z calcd for C21H19FN2O3: 366.1380, found 366.1380.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07666888B2 |
| Source dataset | uspto-grants-2010_02 |
| ORD ID | ord-ca680add4033459f9bd46f1d710f1c70 |
| Source note | uspto-grants-2010_02 |