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

HRID 2183458

反応式

HRID 2183458 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
145 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0bf77f5291be4eca96399512bad071f4
出典データセット
uspto-grants-2005_05
特許番号
US06900210B2

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