Methanol → Tert-butyl 2-(1-methylpiperidin-4-yl)hydrazinecarboxylate

HRID 1530649

반응식

HRID 1530649 반응식
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[N:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:4][CH2:3]1.CC(C[AlH]CC(C)C)C.CO.O>C1COCC1>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([NH:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:7]1

참가 물질

6

반응물 4

HCID 887MethanolHCID 962WaterHCID 14487Diisobutylaluminum hydrideHCID 21097379Tert-butyl 2-(1-methylpiperidin-4-ylidene)hydrazinecarboxylate

생성물 1

HCID 68313226Tert-butyl 2-(1-methylpiperidin-4-yl)hydrazinecarboxylate수율 69.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

To a solution of tert-butyl 2-(1-methylpiperidin-4-ylidene)hydrazinecarboxylate (500 mg, 2.20 mmol) in THF (50 mL) was added DIBAl-H (22 mL, 22 mmol) under nitrogen atmosphere. The resulting mixture was stirred at 25° C. overnight. Methanol (5 mL) was added to quench the reaction at −78° C. After being stirred at room temperature for 1 h, water (10 mL) was added. The solid was filtered off and washed with EtOAc. The combined filtrate was partitioned and extracted with EtOAc (3×50 mL), dried over Na2SO4, and concentrated. The residue was purified by silica gel chromatography eluting with EtOAc/petroleum ether (1:10) to give tert-butyl 2-(1-methylpiperidin-4-yl)hydrazinecarboxylate (350 mg, 69% yield) as a colorless oil. LCMS (ESI) m/z: 230.4 [M+H+].

후처리

  1. customto quench
  2. customthe reaction at −78° C
  3. stirringAfter being stirred at room temperature for 1 h
  4. filtrationThe solid was filtered off
  5. washwashed with EtOAc
  6. customThe combined filtrate was partitioned
  7. extractionextracted with EtOAc (3×50 mL)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel chromatography
  11. washeluting with EtOAc/petroleum ether (1:10)

출처 및 근거

ORD 기록
ord-85c9a7c1b86540e0a58e0307bac4a0ed
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090628B2

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