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

HRID 1529299Notes

Reaction equation

HRID 1529299 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-a934b76bac0f4d45bb9660122d99265e
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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