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

HRID 1253758노트

반응식

HRID 1253758 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%

후처리

  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)

출처 및 근거

ORD 기록
ord-8a02c1fad1c04ce89971ad086e548559
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455475B2

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