Ethanol → Methyl 1-(5-aminopyridin-2-yl)-4-methylpiperidine-4-carboxylate

HRID 1713903노트

반응식

HRID 1713903 반응식
[CH3:1][C:2]1([C:17]([O:19][CH3:20])=[O:18])[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][N:9]=2)[CH2:4][CH2:3]1.CCO>[Pd].C1COCC1>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]([N:5]2[CH2:6][CH2:7][C:2]([CH3:1])([C:17]([O:19][CH3:20])=[O:18])[CH2:3][CH2:4]2)=[N:9][CH:10]=1

참가 물질

5

반응물 2

HCID 702EthanolHCID 59464275Methyl 4-methyl-1-(5-nitropyridin-2-yl)piperidine-4-carboxylate

생성물 1

HCID 59464146Methyl 1-(5-aminopyridin-2-yl)-4-methylpiperidine-4-carboxylate수율 100%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of methyl 4-methyl-1-(5-nitropyridin-2-yl)piperidine-4-carboxylate (3.32 g, 11.89 mmol) in abs EtOH (200 mL) and THF (200 mL) was added 10% Pd/C (400 mg) and then the reaction mixture was evacuated with hydrogen (5 cycles) and allowed to stir at ambient temperature overnight. The reaction mixture was filtered and then concentrated and the black residue purified on a 120 g silica Crawford silicyle cartridge loading in 40% EtOAc/isohexane with some DCM and eluting a gradient of 40-80% EtOAc using an Isco companion to provide the title compound (2.96 g, 11.89 mmol, 100%).

후처리

  1. customthe reaction mixture was evacuated with hydrogen (5 cycles)
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated
  4. customthe black residue purified on a 120 g silica Crawford silicyle cartridge loading in 40% EtOAc/isohexane with some DCM
  5. washeluting a gradient of 40-80% EtOAc using an Isco companion

출처 및 근거

ORD 기록
ord-4db8e991b6b148c78fb7e1806b1e112f
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795283B2

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