Benzenepropanal → HCID 57011534, compound

Participants

Reaction Steps

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%).

Provenance & Evidence