Sodium hydride → 9-(Pyridin-4-yl-methyl)-3,9-diazaspiro[5.5]undecane-3-carboxylic acid tert-butyl ester

HRID 1253758ノート

反応式

HRID 1253758 の反応式
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13]2([CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Cl.Br[CH2:23][C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1>CN(C=O)C>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13]2([CH2:20][CH2:19][N:18]([CH2:23][C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[CH2:17][CH2:16]2)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 15296367tert-Butyl 3,9-diazaspiro[5.5]undecane-3-carboxylateHCID 222741514-(Bromomethyl)pyridine hydrochloride

生成物 1

HCID 595055469-(Pyridin-4-yl-methyl)-3,9-diazaspiro[5.5]undecane-3-carboxylic acid tert-butyl ester収率 35%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

NaH (60% strength in mineral oil, 709 mg, 29.52 mmol) was added to a mixture of 3,9-diazaspiro[5.5]undecane-3-carboxylic acid tert-butyl ester (2.5 g, 9.84 mmol) in DMF (50 ml) at 0° C., the mixture was stirred at room temperature for 2 h, 4-(bromomethyl)-pyridine HCl (2.42 mg, 14.76 mmol) was then added and the mixture was stirred at room temperature for 16 h. Finally, ice was added and the reaction mixture was extracted with ethyl acetate. The combined organic phases were washed with water and sat. NaCl solution, dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (mobile phase methanol/methylene chloride). Yield: 35%

後処理

  1. stirringthe mixture was stirred at room temperature for 16 h
  2. additionFinally, ice was added
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe combined organic phases were washed with water and sat. NaCl solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography (mobile phase methanol/methylene chloride)

出典と根拠

ORDレコード
ord-8a02c1fad1c04ce89971ad086e548559
出典データセット
uspto-grants-2013_06
特許番号
US08455475B2

反応ノート

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