HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → HCID 45786893, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 2-Chloro-5-nitropyridine | HCID 78308 | — |
| Reactant | Tert-butyl 4-hydroxypiperidine-1-carboxylate | HCID 643502 | — |
| Reactant | Potassium bis(trimethylsilyl)amide | HCID 3251421 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 45786893 | HCID 45786893 | — |
Reaction Steps
To a solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (1 eq) in DMF was added potassium bis-trimethylsilylamide (1.5 eq, 1M solution in tetrahydrofuran). The solution was stirred at room temperature for 10 minutes, and 2-chloro-5-nitropyridine (1.2 eq) was added. The reaction mixture was submitted to microwave irradiation for 600 seconds at 145° C. EtOAc and water were added to the reaction and the layers separated. The organic layer was washed with water, brine, dried over sodium sulfate and evaporated to give brown crude material. Purification by silica gel column chromatography using 10% EtOAc/hexane afforded the product as a light yellow solid. LC/MS (m/z): 324.3 (MH+), Rt 3.33 minutes
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08563549B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-21a398a43bbe45a69c13867e456f3b9e |
| Source note | uspto-grants-2013_10 |