HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 1-(tert-Butoxycarbonyl)-4-(p-toluenesulfonyloxy)piperidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 4-Toluenesulfonyl chloride | HCID 7397 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Tert-butyl 4-hydroxypiperidine-1-carboxylate | HCID 643502 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | 1-(tert-Butoxycarbonyl)-4-(p-toluenesulfonyloxy)piperidine | HCID 15734713 | 76.4% |
Reaction Steps
1-(tert-Butoxycarbonyl)-4-hydroxypiperidine (4.81 g) was dissolved in pyridine (48 ml), added with p-toluenesulfonyl chloride (9.0 g) and triethylamine (6.7 ml) and stirred at room temperature for 17 hours. The reaction mixture was added with cold water (500 ml) and stirred for 2 hours, and then the produced crystals were collected by filtration. These crystals were purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=3:1) to obtain 6.49 g of the title compound. Yield: 76%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06916822B2 |
| Source dataset | uspto-grants-2005_07 |
| ORD ID | ord-53874a781c2447ac9cf83e9c89d33c4d |
| Source note | uspto-grants-2005_07 |