HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 1-{[3-(4-Methoxyphenyl)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 | 3-(4-Methoxyphenyl)isoxazole-4-carboxylic acid | HCID 59170121 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 1-{[3-(4-Methoxyphenyl)isoxazol-4-yl]carbonyl}-5-methyl-3-phenylpyrrolidin-3-ol | HCID 59170093 | 52.9% |
Reaction Steps
A solution of 3-(4-methoxyphenyl)isoxazole-4-carboxylic acid (7 mg, 0.03 mmol), N-ethyl-N-isopropylpropan-2-amine (16 μL, 0.09 mmol, 3 equ.) and TBTU (12 mg, 0.036 mmol, 1.2 equ.) in DMF (0.3 mL) was added to 5-methyl-3-phenylpyrrolidin-3-ol (5 mg, 0.03 mmol). After 1 h at rt the crude product was purified by RP-HPLC. The pure fractions were basified (NaHCO3) and extracted with ethyl acetate, dried (Na2SO4), evaporated and dried in vacuum to yield the title compound (6 mg). MS (ESI, pos. ion) m/z: calcd for C22H22N2O4: 378.1580, found 378.1580.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07666888B2 |
| Source dataset | uspto-grants-2010_02 |
| ORD ID | ord-4adbe9649d6d4cdd910d77ee46dc74d4 |
| Source note | uspto-grants-2010_02 |