Pyridine → (S)-{1-[3-(6-Methyl-pyridin-3-yloxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester

HRID 2183458

반응식

HRID 2183458 반응식
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12](Br)[CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[OH:18][C:19]1[CH:20]=[CH:21][C:22]([CH3:25])=[N:23][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].N1C=CC=CC=1>[Cu](I)I.C(N(CC)CC)C.CCOC(C)=O>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:18][C:19]2[CH:24]=[N:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]

참가 물질

8

반응물 4

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 142752-Methyl-5-hydroxypyridineHCID 56971804(S)-N-Boc-1-(3-bromophenyl)ethylamine

생성물 1

HCID 60004122(S)-{1-[3-(6-Methyl-pyridin-3-yloxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester수율 33%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

반응 조건

온도
145 °C

실험 절차

A mixture of (S)-[1-(3-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (10 g, 33.3 mol), 5-hydroxy-2-methylpyridine (4 g, 36.7 mol), copper iodide (6.3 g, 33.3 mol), potassium carbonate (9.2 g, 66.7 mol) and pyridine (33 mL) in sealed tube was heated at 145° C. for six days. The reaction was cooled down to room temperature and filtered, the filtrate was washed with H2O and extracted with CH2Cl2 three times, and the combined organic layers were dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with 30:20:1/Hexane:EtOAc:triethylamine to give the title product (3.8 g, 33% yield) as sticky yellow oil.

후처리

  1. temperatureThe reaction was cooled down to room temperature
  2. filtrationfiltered
  3. washthe filtrate was washed with H2O
  4. extractionextracted with CH2Cl2 three times
  5. dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel eluting with 30:20:1/Hexane

출처 및 근거

ORD 기록
ord-0bf77f5291be4eca96399512bad071f4
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06900210B2

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