Triethylamine → 2-Bromo-5-isopropyl-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 (5.00 g) was suspended in dichloromethane (200 ml), and to the suspension triethylamine (4.16 ml) was added, and the mixture was stirred at room temperature into a solution. Acetic acid (2.55 ml) and acetone (17 ml) were added to the reaction mixture, and the mixture was stirred at room temperature for 2 minutes. Sodium triacetoxyborohydride (19.1 g) was added to the reaction mixture, and the resultant mixture was stirred at room temperature for 5 hours. A 3N aqueous solution (200 ml) of sodium hydroxide was added to the reaction mixture to separate an organic layer. 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 (3.45 g) as a yellow oil.

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