4-(5-Benzyloxy-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester → 4-(5-Hydroxy-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester

HRID 2355623노트

반응식

HRID 2355623 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21]CC3C=CC=CC=3)=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][N:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 1

HCID 674007704-(5-Benzyloxy-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 674009714-(5-Hydroxy-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester수율 75.4%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

To a solution of 4-(5-benzyloxy-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (18.2 g, 47.5 mmol, 1.0 equiv) in methanol (200 mL) was added 10% Pd on activated carbon (2.53 g, 2.38 mmol 0.05 equiv) under an atmosphere of Ar. The reaction vessel was twice evacuated and ventilated with hydrogen gas and the well stirred reaction mixture was subsequently hydrogenated at rt and 1 bar H2 for 3 h. After filtration over dicalite the crude reaction mixture was concentrated by evaporation under reduced pressure and purified by column chromatography on silica eluting with a gradient of dichloromethane/methanol to give 10.50 g (75%) of the title compound as a light yellow solid. MS (ISP): 294.2 [M+H]+.

후처리

  1. customThe reaction vessel was twice evacuated
  2. customreaction mixture
  3. customwas subsequently hydrogenated at rt
  4. filtrationAfter filtration over dicalite the crude
  5. customreaction mixture
  6. concentrationwas concentrated by evaporation under reduced pressure
  7. custompurified by column chromatography on silica eluting with a gradient of dichloromethane/methanol

출처 및 근거

ORD 기록
ord-f4265ba3512b42e4bde1b59deb24b5ac
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07754744B2

반응 노트

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