Sodium hydride → (R)-tert-butyl 3-(6-chloropyrazin-2-yloxy)piperidine-1-carboxylate

HRID 1529299Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1529299
[OH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[H-].[Na+].[Cl:17][C:18]1[CH:23]=[N:22][CH:21]=[C:20](Cl)[N:19]=1>CN(C=O)C>[Cl:17][C:18]1[N:19]=[C:20]([O:1][C@@H:2]2[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]2)[CH:21]=[N:22][CH:23]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 785042,6-DichloropyrazineHCID 1514398(R)-1-Boc-3-hydroxypiperidine

Produkt 1

HCID 57502428(R)-tert-butyl 3-(6-chloropyrazin-2-yloxy)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a 500-mL round-bottomed flask was added (R)-tert-butyl 3-hydroxypiperidine-1-carboxylate (2.5 g, 12.42 mmol) in DMF (80 mL) at 0° C. NaH (1.080 mL, 24.84 mmol) was added slowly and the mixture was stirred at 0° C. for 15 min. 2,6-dichloropyrazine (1.851 g, 12.42 mmol) was added and the mixture was warmed to RT and stirred for 2 h. The reaction mixture was quenched with water and extracted with DCM. The combined organic layers were washed with water, brine, dried, filtered and concentrated to give the crude title compound. The material was used in the next step without further purification

Aufarbeitung

  1. temperaturethe mixture was warmed to RT
  2. stirringstirred for 2 h
  3. customThe reaction mixture was quenched with water
  4. extractionextracted with DCM
  5. washThe combined organic layers were washed with water, brine
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a934b76bac0f4d45bb9660122d99265e
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090593B2

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