Water → HCID 69022697, compound

Reaction equation

[BH4-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[N:9]([CH3:29])[CH:10]=[C:11]([C:27]#[N:28])[C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH:25]=[O:26])=[CH:15][CH:14]=1)=[O:7])[CH3:4].O>CO>[CH2:3]([O:5][C:6]([C:8]1[N:9]([CH3:29])[CH:10]=[C:11]([C:27]#[N:28])[C:12]=1[C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH2:25][OH:26])=[CH:17][CH:18]=1)=[O:7])[CH3:4]

Participants

Procedure

Add sodium borohydride (0.79 g, 2.1 mmol) to 4-cyano-3-(2′-formyl-biphenyl-4-yl)-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (0.50 g, 1.40 mmol, prepared in example E-23) in methanol at 0° C. with stirring. After 1 hour, allow the reaction mixture to warm to ambient temperature. After 2 hours, pour the reaction mixture into water and extract with ethyl acetate. Combine the organic extracts, wash with water and brine, dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Purify the residue by flash chromatography eluting with ethyl acetate:hexane to provide the title compound. Mass spectrum: EI+=360.2