HuagongsheHuagongshe Chemistry Print Report · For research reference only
tert-Butyl 4-oxopiperidine-1-carboxylate → Tert-butyl 4-(8-chloro-1,5-naphthyridin-3-yl)-4-hydroxypiperidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | tert-Butyl 4-oxopiperidine-1-carboxylate | HCID 735900 | — |
| Reactant | 3-Bromo-8-chloro-1,5-naphthyridine | HCID 13459137 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Tert-butyl 4-(8-chloro-1,5-naphthyridin-3-yl)-4-hydroxypiperidine-1-carboxylate | HCID 57691287 | 38% |
Reaction Conditions
| Temperature | -78 °C |
|---|
Reaction Steps
Dissolved 3-bromo-8-chloro-1,5-naphthyridine (210 mg, 862 μmol) in 8 mL of THF and cooled to −78° C. Then added butyllithium (517 μl, 1294 μmol) and stirred for 15 min. Added tert-butyl 4-oxopiperidine-1-carboxylate (258 mg, 1294 μmol) and let warm to room temperature over 1 h. The reaction was quenched with saturated NH4Cl and extracted with dichloromethane (3×20 mL), dried over NaSO4 and concentrated. Intermediate was purified via MPLC (DCM/MeOH/NHOH) to yield tert-butyl 4-(8-chloro-1,5-naphthyridin-3-yl)-4-hydroxypiperidine-1-carboxylate (120 mg, 38% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08217177B2 |
| Source dataset | uspto-grants-2012_07 |
| ORD ID | ord-73b4c21e112c43e380220106d5ab7821 |
| Source note | uspto-grants-2012_07 |