HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methylmorpholine → Tert-butyl 2-[[(4-bromobenzoyl)amino]methyl]pyrrolidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | 4-Bromobenzoic acid | HCID 11464 | — |
| Reactant | (+-)-2-(Aminomethyl)-1-N-Boc-pyrrolidine | HCID 2756484 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Tert-butyl 2-[[(4-bromobenzoyl)amino]methyl]pyrrolidine-1-carboxylate | HCID 58185404 | 100% |
Reaction Steps
To 2-aminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1.00 g, 4.97 mmol) and 4-bromo-benzoic acid (996 mg, 4.97 mmol) in DMF (25 mL) was added N-methylmorpholine (655 μl, 5.96 mmol) and HATU (1.89 g, 4.97 mmol). After stirring for 3 hours the reaction was concentrated then diluted with EtOAc and washed with 1N HCl, saturated NaHCO3, and brine. The organic phase was then dried over Na2SO4 and concentrated. The crude material was purified by silica gel chromatography (20-50% EtOAc-hexanes gradient) to afford 2-[(4-bromo-benzoylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (1.91 g, 4.97 mmol, quantitative yield). LCMS-ESI+: calc'd for C17H24BrN2O3: 383.1 (M+H+). Found: 383.6 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08822430B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-10725b784f7e497a9e5b5020e59d3d3c |
| Source note | uspto-grants-2014_09 |