HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → ((4R)-1-{[5-(4-methylphenyl)isoxazol-4-yl]carbonyl}-4-phenylpyrrolidin-3-yl)methanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | (4-Phenylpyrrolidin-3-yl)methanol | HCID 13316928 | — |
| Reactant | 5-(p-Tolyl)isoxazole-4-carboxylic acid | HCID 22831706 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | ((4R)-1-{[5-(4-methylphenyl)isoxazol-4-yl]carbonyl}-4-phenylpyrrolidin-3-yl)methanol | HCID 68684409 | 33.4% |
Reaction Steps
A solution of (4-phenylpyrrolidin-3-yl)methanol (7 mg, 0.033 mmol), TBTU (13 mg, 0.039 mmol, 1.2 equ.) and N-ethyl-N-isopropylpropan-2-amine (11 μL, 0.066 mmol, 2 equ.) in DMF (0.3 mL) was added to 5-(4-methylphenyl)isoxazole-4-carboxylic acid (7 mg, 0.033 mmol) and the reaction mixture was stirred 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 (4 mg). MS (ESI, pos. ion) m/z calcd for C22H22N2O3: 362.1630, found 362.1629.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07666888B2 |
| Source dataset | uspto-grants-2010_02 |
| ORD ID | ord-de973918f5334992b12fc13abd8e2201 |
| Source note | uspto-grants-2010_02 |