Acetaldehyde → HCID 86632927, compound

HRID 1398945Notes

Reaction equation

HRID 1398945 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]([CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[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:32](=O)[CH3:33].[C:35](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:36].[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][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:28])([CH3:30])[CH3:29])[C:7]2[C:2]([N:1]([CH2:32][CH3:33])[CH2:35][CH3:36])=[CH:3][CH:4]=[CH:5][C:6]=2[N:10]=1

Participants

8

Reactant 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86632926HCID 86632926, compound

Product 1

HCID 86632927HCID 86632927, compoundYield 90.4%

Reagents, catalysts & solvents 4

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

Procedure

To a solution of tert-butyl (3-{7-amino-2-[(2,4-dichlorophenyl)(hydroxy)methyl]-1H-benzimidazol-1-yl}propyl)carbamate (3.00 g, 6.45 mmol) in methanol (65 mL) and acetic acid (3.3 mL) was added acetoaldehyde (2.41 mL, 38.7 mmol) at 0° C. The resultant mixture was stirred at 0° C. for 30 min. To the reaction mixture was added sodium triacetoxyborohydride (8.20 g, 38.7 mmol) at 0° C. After the resultant mixture was stirred at 0° C. for 3 h, the mixture was diluted with aqueous sodium hydrogen carbonate and 1N aqueous sodium hydroxide, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a ethyl acetate to give a crude solid, which was washed with diisopropyl ether to give the title compound as a colorless solid (3.04 g, 5.83 mmol, 90%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with 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 ethyl acetate
  7. customto give a crude solid, which
  8. washwas washed with diisopropyl ether

Sources & evidence

ORD record
ord-8cd5933f096d4c24b6561466228843f4
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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