Sodium borohydride → [6-(1H-Imidazol-1-yl)pyridin-3-yl]methanol

Reaction equation

[BH4-].[Na+].[N:3]1([C:8]2[CH:17]=[CH:16][C:11]([C:12](OC)=[O:13])=[CH:10][N:9]=2)[CH:7]=[CH:6][N:5]=[CH:4]1>CO.O>[N:3]1([C:8]2[CH:17]=[CH:16][C:11]([CH2:12][OH:13])=[CH:10][N:9]=2)[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

Procedure

NaBH4 (37.82 g) is added portionwise to a suspension of the imidazolyl ester of Step 2. above (9.98 g) in methanol at about 0.° C. The reaction mixture is heated to reflux for 71/2 hours, allowed to cool and stand 15 hours. Water (75 ml) is added, and the quenched reaction mixture evaporated, affording a solid residue which is suspended in water, extracted with chloroform dried over Na2SO4, filtered and evaporated, recrystallized (CHCl3), affording the desired product as a white solid. M.P.=128.5°-130° C.