Acetic Acid → N-(4-Chlorobenzyl)-2-(hydroxymethyl)-4-methyl-7-oxo-3-{[2-(trimethylsilyl)ethoxy]methyl}-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Participants

Reaction Steps

To a cold (0° C.), stirred solution of 1.56 g of N-(4-chlorobenzyl)-2-formyl-4-methyl-7-oxo-3-{[2-(trimethylsilyl)ethoxy]methyl}-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide And 0.91 mL of acetic acid in 32 mL of CH2Cl2 is added 1.7 g of sodium triacetoxyborohydride. The ice bath is removed and the reaction allowed to stir at room temperature for 4 h, then partitioned between chloroform and aq. NaHCO3. The organic phase is dried (Na2SO4) and concentrated under reduced pressure, and the residue flash chromatographed on silica using 2% MeOH in CH2Cl2 to provide 1.53 g of the title compound as a pale yellow solid. Recrystallization from acetonitrile furnishes white platelets.

Provenance & Evidence