Formaldehyde → 2-Bromo-5-methyl-4,5,6,7-tetrahydrothiazolo(5,4-c)pyridine

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Reaction Steps

2-Bromo-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine trifluoroacetate (422 mg) was suspended in dichloromethane (10 ml), triethylamine (0.356 ml) was added, and the mixture was stirred at room temperature for 15 minutes. Acetic acid (0.216 ml) and an aqueous solution (35% solution, 0.202 ml) of formaldehyde were added to the reaction mixture, and the resultant mixture was stirred at room temperature for 2 minutes. Sodium triacetoxyborohydride (428 mg) was added to the reaction mixture, and the resultant mixture was stirred at room temperature for 1 hour. A 1N aqueous solution (10 ml) of sodium hydroxide was added to the reaction mixture and an organic layer was separated. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=100:1) to obtain the title compound (286 mg) as a pale brown oil.

Provenance & Evidence