HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 1-[(5-Benzylisoxazol-4-yl)carbonyl]-3-phenylpyrrolidin-3-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 3-Phenylpyrrolidin-3-ol hydrochloride | HCID 200280 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | 5-Benzyl-4-isoxazolecarboxylic acid | HCID 14787252 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 1-[(5-Benzylisoxazol-4-yl)carbonyl]-3-phenylpyrrolidin-3-ol | HCID 59170118 | 23% |
Reaction Steps
A solution of 5-benzylisoxazole-4-carboxylic acid (10 mg, 0.05 mmol), TBTU (19 mg, 0.06 mmol, 1,2 equ.) and N-ethyl-N-isopropylpropan-2-amine (17 μL, 0.10 mmol, 2 equ) in DMF (0.3 mL) was added to 3-phenylpyrrolidin-3-ol hydrochloride (10 mg, 0.05 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 (4 mg). MS (ESI, pos. ion) m/z calcd for C21H20N2O3: 348.1474, found 348.1481.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07666888B2 |
| Source dataset | uspto-grants-2010_02 |
| ORD ID | ord-500eb554a7344b95aba94592e2179daf |
| Source note | uspto-grants-2010_02 |