HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sulfuric Acid → 1-(tert-Butoxycarbonyl)-4-(p-toluenesulfonyloxy)piperidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | 4-Toluenesulfonyl chloride | HCID 7397 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Tert-butyl 4-hydroxypiperidine-1-carboxylate | HCID 643502 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-(tert-Butoxycarbonyl)-4-(p-toluenesulfonyloxy)piperidine | HCID 15734713 | — |
Reaction Steps
201 g tert-Butyl 4-hydroxypiperidine-1-carboxylate, 160 ml triethylamine and 6.0 g 4-dimethylaminopyridine are dissolved in 750 ml DCM. 191 g 4-toluenesulfonylchloride is added and the mixture is refluxed for 7 h. The mixture is cooled in ice and acidified with 100 ml of 1M H2SO4; the organic layer is washed with 300 ml of water (twice), 250 ml of 1 M Na2CO3 solution (twice), dried over MgSO4, filtered and concentrated in vacuo.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09340522B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-5b9ca234c2894b6b9aaf385c1982d255 |
| Source note | uspto-grants-2016_05 |