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Trimethylsilyl iodide → (3S,6R)-3-amino-6-(tert-butyl-dimethyl-silanyloxy)-1-pyridin-3-ylmethyl-azepan-2-one

HRID 2224020
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HRID 2224020 반응식
C(OC(=O)[NH:7][C@H:8]1[CH2:14][CH2:13][C@@H:12]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH2:11][N:10]([CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[C:9]1=[O:30])(C)(C)C.C[Si](I)(C)C>C(Cl)Cl>[NH2:7][C@H:8]1[CH2:14][CH2:13][C@@H:12]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH2:11][N:10]([CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[C:9]1=[O:30]
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참가 물질

4

반응물 2

HCID 85247Trimethylsilyl iodideHCID 69268061[(3S,6R)-6-(tert-butyl-dimethyl-silanyloxy)-2-oxo-1-pyridin-3-ylmethyl-azepan-3-yl]-carbamic acid tert-butyl ester

생성물 1

HCID 69267176(3S,6R)-3-amino-6-(tert-butyl-dimethyl-silanyloxy)-1-pyridin-3-ylmethyl-azepan-2-one수율 92.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a stirred solution of [(3S,6R)-6-(tert-butyl-dimethyl-silanyloxy)-2-oxo-1-pyridin-3-ylmethyl-azepan-3-yl]-carbamic acid tert-butyl ester (5.0 g, 11.1 mmol) in CH2Cl2 (50 mL) at −78° C. is added trimethylsilyl iodide (2.8 g, 14.0 mmol) neat. After 30 min the reaction solution is warmed to 0° C. and stirred for 15 min. The reaction is quenched with a solution of CH3OH (25 mL) and NH4HCO3 (10 mL, saturated in H2O), and partitioned with H2O/CH2Cl2. The CH2Cl2 fraction is dried over Na2SO4 and evaporated to a gum and chromatographed on silica (95% CH2Cl2/5% CH3OH) to give 3.6 g (92.6%) of (3S,6R)-3-amino-6-(tert-butyl-dimethyl-silanyloxy)-1-pyridin-3-ylmethyl-azepan-2-one as a white solid. MS (ESI) 350.2 (M+H)+

후처리

  1. customThe reaction is quenched with a solution of CH3OH (25 mL) and NH4HCO3 (10 mL, saturated in H2O)
  2. custompartitioned with H2O/CH2Cl2
  3. dry with materialThe CH2Cl2 fraction is dried over Na2SO4
  4. customevaporated to a gum
  5. customchromatographed on silica (95% CH2Cl2/5% CH3OH)

출처 및 근거

ORD 기록
ord-02379aae9dd446a3a86beb809d56365a
출처 데이터셋
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07378410B2

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