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Sodium hydride → 1,1-Dimethylethyl 2,6-dihydro-2-[[2-(trimethylsilyl)ethoxy]methyl]pyrrolo[3,4-c]pyrazole-5(4H)-carboxylate

HRID 532525
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HRID 532525 반응식
[N:1]1[NH:2][CH:3]=[C:4]2[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][C:5]=12.[H-].[Na+].[CH3:18][Si:19]([CH3:26])([CH3:25])[CH2:20][CH2:21][O:22][CH2:23]Cl>CN(C=O)C>[CH3:18][Si:19]([CH3:26])([CH3:25])[CH2:20][CH2:21][O:22][CH2:23][N:2]1[CH:3]=[C:4]2[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][C:5]2=[N:1]1
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참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178451520HCID 178451520, 화합물

생성물 1

HCID 679578031,1-Dimethylethyl 2,6-dihydro-2-[[2-(trimethylsilyl)ethoxy]methyl]pyrrolo[3,4-c]pyrazole-5(4H)-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of tert-butyl 2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate (20 g, 96 mmol) in DMF (200 mL) at 0° C. was added sodium hydride (4.21 g, 105 mmol). After stirring for 1 h at RT, 2-trimethylsilylethoxymethyl chloride (SEM-Cl) (4.65 mL, 26.3 mmol) was added. The resulting mixture was stirred at RT overnight. The mixture was quenched with saturated NH4OH, and the solvents were removed. The residue was diluted with ethyl acetate (500 mL), washed with water, brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on a silica gel Biotage 65i® column, eluting with 0 to 20% ethyl acetate in hexanes to give the title compound as a colorless gum. LC-MS: 340.1 (M+H)

후처리

  1. stirringThe resulting mixture was stirred at RT overnight
  2. customThe mixture was quenched with saturated NH4OH
  3. customthe solvents were removed
  4. additionThe residue was diluted with ethyl acetate (500 mL)
  5. washwashed with water, brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on a silica gel Biotage 65i® column
  9. washeluting with 0 to 20% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-d1d2d32527ad42d3b2614fe588a29aeb
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08853212B2

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