Acetaldehyde → HCID 86632922, compound

HRID 1628582Notes

Reaction equation

HRID 1628582 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]([CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:9]([CH:11]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[OH:12])=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:31](=O)[CH3:32].[C:34](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:35].[Na+]>CO.C(O)(=O)C.C(=O)([O-])O.[Na+].[OH-].[Na+]>[Cl:20][C:14]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=1[CH:11]([OH:12])[C:9]1[N:8]([CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:29])[CH3:28])[C:7]2[C:2]([N:1]([CH2:31][CH3:32])[CH2:34][CH3:35])=[CH:3][CH:4]=[CH:5][C:6]=2[N:10]=1

Participants

8

Reactant 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86632921HCID 86632921, compound

Product 1

HCID 86632922HCID 86632922, compoundYield 74%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 14798Sodium HydroxideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of tert-butyl (2-{7-amino-2-[(2,4-dichlorophenyl) (hydroxy)methyl]-1H-benzimidazol-1-yl}ethyl)carbamate (5.00 g, 11.1 mmol) in methanol (110 mL) and acetic acid (5.5 mL) was added acetoaldehyde (4.15 mL, 66.6 mmol) at 0° C. The resultant mixture was stirred at 0° C. for 30 min. To the reaction mixture was added sodium triacetoxyborohydride (14.1 g, 66.5 mmol) at 0° C. After the resultant mixture was stirred at room temperature for 3 h, the mixture was diluted with aqueous sodium hydrogen carbonate and 8N aqueous sodium hydroxide, and extracted with ethyl acetate. The combined organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a 20-50% ethyl acetate/n-hexane gradient mixture to give a colorless solid (4.15 mg, 8.18 mmol, 74%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with a 20-50% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-31765e9c856a41ef94bf87c767e135bb
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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