HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 1-{[5-(4-Fluorophenyl)isoxazol-4-yl]carbonyl}-5-methyl-3-phenylpyrrolidin-3-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | 5-Methyl-3-phenyl-pyrrolidin-3-ol | HCID 3051395 | — |
| Reactant | 5-(4-Fluorophenyl)isoxazole-4-carboxylic acid | HCID 3723375 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 1-{[5-(4-Fluorophenyl)isoxazol-4-yl]carbonyl}-5-methyl-3-phenylpyrrolidin-3-ol | HCID 59170187 | 75.1% |
Reaction Steps
N-ethyl-N-isopropylpropan-2-amine (14 μL, 0.04 mmol) was added to a solution of 5-(4-fluorophenyl)isoxazole-4-carboxylic acid (8 mg, 0.04 mmol), 5-methyl-3-phenylpyrrolidin-3-ol (7 mg, 0.04 mmol) and TBTU (15 mg, 0.048 mmol, 1.2 equ.) in DMF (0.3 mL) at rt. The reaction mixture was left at rt for 2 h. The crude product was purified by RP-HPLC. After evaporation of the solvents the product was dried in vacuum to yield the title compound (11 mg). MS (ESI, pos. ion) m/z: calcd for C21H19FN2O3: 366.1380, found 366.1391.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07666888B2 |
| Source dataset | uspto-grants-2010_02 |
| ORD ID | ord-ed704f59dab74532b17c695f4378ca94 |
| Source note | uspto-grants-2010_02 |