HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → Tert-butyl 6-(pyrrolidin-1-ylmethyl)pyridin-2-ylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | (6-(Tert-butoxycarbonylamino)pyridin-2-yl)methyl methanesulfonate | HCID 19349110 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | Tert-butyl 6-(pyrrolidin-1-ylmethyl)pyridin-2-ylcarbamate | HCID 66694553 | 84.5% |
Reaction Steps
A mixture of (6-(tert-butoxycarbonylamino)pyridin-2-yl)methyl methanesulfonate 79 (1.30 g, 3.2 mmol), pyrrolidine 68 (0.46 g, 6.4 mmol) and K2CO3 (1.30 g, 9.6 mmol) in acetonitrile (15 mL) was stirred at room temperature for 12 h. Saturated aqueous NaHCO3 was added and the mixture was concentrated under reduced pressure. The resulting aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to afford 80 (0.75 g, 62% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09326986B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-cd60a7e88b1b4db19c874efd1d53601b |
| Source note | uspto-grants-2016_05 |