HuagongsheHuagongshe Chemistry Print Report · For research reference only
Nitrogen → Methanesulfonic acid 4-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-2-ylmethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | [4-(2-Methyl-[1,3]dioxolan-2-yl)-pyridin-2-yl]-methanol | HCID 66929049 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Methanesulfonic acid 4-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-2-ylmethyl ester | HCID 86649481 | — |
Reaction Steps
In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [4-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-2-yl]-methanol (950 mg, 4.87 mmol) in dry CH2Cl2 (5 mL) was treated at 0° C. with Et3N (0.88 mL, 6.29 mmol) followed by DMAP (60 mg, 0.49 mmol) and Ms-Cl (0.49 mL, 6.15 mmol). After stirring at rt for 2 h, the reaction was quenched with water (5 mL). The org. layer was dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (5:1 to 2:1 hept-EA) gave the title compound as a yellow oil. LC-MS-conditions 02: tR=0.76 min, [M+H]+=274.30.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08536209B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-2384e6599ea749259f56e9210bce5bba |
| Source note | uspto-grants-2013_09 |