HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyrrolidine → 3-Methyl-3-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 1-((Tert-butoxy)carbonyl)-3-methylpyrrolidine-3-carboxylic acid | HCID 53255455 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-Methyl-3-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylic acid tert-butyl ester | HCID 59605630 | 78% |
Reaction Steps
To a solution of 3-methylpyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (348 mg, 1.52 mmol) in DMF (10 mL) were added DIPEA (0.53 mL, 3.04 mmol), pyrrolidine (0.25 mL, 3.04 mmol) and HATU (693 mg, 1.82 mmol). The reaction mixture was stirred at room temperature for 18 hours and then partitioned between water and EtOAc. The organic layer was separated and washed with a 0.1N aqueous HCl solution and brine, dried over Na2SO4, filtered and concentrated to give the desired product as a white solid (334 mg, 78%). 1H NMR (400 MHz, CHCl3-d): δ 3.61-3.38 (m, 8H); 2.00-1.79 (m, 6H); 1.47-1.44 (m, 9H); 1.33 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08173650B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-63fcf17a01c84a6bbb13c83d7b13da43 |
| Source note | uspto-grants-2012_05 |