HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Hydroxyquinoline → tert-butyl{1-[2-(2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Hydroxyquinoline | HCID 6038 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2-(4-((Tert-butoxycarbonyl)amino)piperidin-1-yl)ethyl methanesulfonate | HCID 56834478 | — |
| Reactant | tert-butyl{1-[2-(7-fluoro-2-oxoquinoxalin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate | HCID 59397942 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | tert-butyl{1-[2-(2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate | HCID 86642648 | 35% |
Reaction Steps
Quinolin-2(1H)-one (250 mg, 1.7 mmol) was deprotonated with sodium hydride (60% in oil, 70 mg, 1.7 mmol) and alkylated with 2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}ethyl methanesulfonate (Intermediate 6) (1.7 mmol) as described for Intermediate 141. Chromatography on silica gel with 0-5% methanol in dichloromethane gave 220 mg (35%) of product as a colorless solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07875715B2 |
| Source dataset | uspto-grants-2011_01 |
| ORD ID | ord-03405be2da0644e9a6aade0d9190a74c |
| Source note | uspto-grants-2011_01 |