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

HRID 532525Notes

Reaction equation

HRID 532525 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-d1d2d32527ad42d3b2614fe588a29aeb
Source dataset
uspto-grants-2014_10
Patent number
US08853212B2

Reaction notes

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