HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → (S)-tert-butyl 2-(5-(1-methylpyrrolidin-2-yl)pyridin-3-yloxy)ethylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | tert-Butyl N-(2-bromoethyl)carbamate | HCID 4103526 | — |
| Reactant | (S)-5-(1-Methylpyrrolidin-2-yl)pyridin-3-ol | HCID 58537397 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (S)-tert-butyl 2-(5-(1-methylpyrrolidin-2-yl)pyridin-3-yloxy)ethylcarbamate | HCID 58537431 | 34.3% |
Reaction Steps
(S)-5-(1-Methylpyrrolidin-2-yl)pyridin-3-ol (preparation 10) (175 mg, 0.98 mmol), tert-butyl 2-bromoethylcarbamate (550 mg, 2.45 mmol) and potassium carbonate (676 mg, 4.9 mmol) in DMF (7 mL) were heated at 90° C. for 16 hours. The reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate, dried over MgSO4 and evaporated. The crude product was purified by flash chromatography (5%→10% MeOH in DCM) to give the title compound as a yellow oil (108 mg, 34%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08980276B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-f9183f1101484b18b550a9c7b67434f9 |
| Source note | uspto-grants-2015_03 |