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

HRID 1529299노트

반응식

HRID 1529299 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-a934b76bac0f4d45bb9660122d99265e
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090593B2

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