Benzenepropanal → HCID 57011534, compound

HRID 1358489Notes

Reaction equation

HRID 1358489 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][CH2:12][C@@H:13]([N:23]2[CH:27]=[C:26]([C:28]([NH2:30])=[O:29])[N:25]=[CH:24]2)[CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])=[CH:4][CH:3]=1.[CH:31](=O)[CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Si:16]([O:15][CH2:14][C@H:13]([N:23]1[CH:27]=[C:26]([C:28]([NH2:30])=[O:29])[N:25]=[CH:24]1)[CH2:12][CH2:11][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([NH:1][CH2:31][CH2:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH:10]=2)[CH:6]=[CH:7]1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 7707BenzenepropanalHCID 5049666Sodium triacetoxyborohydrideHCID 11224101HCID 11224101, compound

Product 1

HCID 57011534HCID 57011534, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under N2, to a stirred solution of 1-[(R)-4-(6-aminoindol-1-yl)-1-(tert-butyldimethylsilyloxy)-2-butyl]imidazole-4-carboxamide (164 mg, 0.383 mmol) in dichloromethane (10 ml) was added hydrocinnamaldehyde (51 mg, 0.383 mmol) at room temperature. The mixture was stirred for 30 minutes. Sodium triacetoxyborohydride (114 mg, 0.536 mmol) was added to the mixture at room temperature and the resulting mixture was stirred for 5 hours. And then the reaction mixture was partitioned between dichloromethane and water. The organic layer was washed with brine, dried (sodium sulfate), and concentrated in vacuo. The residue was purified by silica gel (10 g) column chromatography eluted with chloroform/methanol (100:1 to 10:1) to give 1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-(3-phenylpropylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide (52.6 mg, 25.2%).

Workup

  1. stirringthe resulting mixture was stirred for 5 hours
  2. customAnd then the reaction mixture was partitioned between dichloromethane and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel (10 g) column chromatography
  7. washeluted with chloroform/methanol (100:1 to 10:1)

Sources & evidence

ORD record
ord-0854f209fa6e4088a666be94e17e03ed
Source dataset
uspto-grants-2003_07
Patent number
US06596738B1

Reaction notes

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