HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 1-(2-Butynyl)-4-[[[4-(2-butynyloxy)phenyl]sulfonyl]methyl]-4-piperidinecarboxylic acid, ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1-Bromo-2-butyne | HCID 2756862 | — |
| Reactant | HCID 22626999 | HCID 22626999 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 1-(2-Butynyl)-4-[[[4-(2-butynyloxy)phenyl]sulfonyl]methyl]-4-piperidinecarboxylic acid, ethyl ester | HCID 86757882 | 85% |
Reaction Steps
A mixture of 4-[[[4-(2-Butynyloxy)phenyl]sulfonyl]methyl]-4-piperidinecarboxylic acid ethyl ester (0.208 g, 0.5 mmol), 1-bromo-2-butyne (0.044 mL 0.53 mmol) and K2CO3 (0.138 g, 1.0 mmol)in 5.0 mL of DMF was stirred at room temperature for 6 h. The reaction was diluted with EtOAc and washed with H2O, brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with EtOAc:hexanes (1:1) to provide 0.183 g (85%) of the desired product as a pale yellow gum. Electrospray Mass Spec: 432.2 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06753337B2 |
| Source dataset | uspto-grants-2004_06 |
| ORD ID | ord-a19148a544b245d2b5f9a139301f95a1 |
| Source note | uspto-grants-2004_06 |