2-Trimethylsilylthiazole → (+/-) 3-((1,3-Thiazol-2-yl)hydroxymethyl)-1-azabicyclo [2.2.2]octane

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Reaction Steps

A mixture of (±) 3-formyl-1-azabicyclo[2.2.2]octane (D32) (2 5g, 0.018 moles) and 2-trimethylsilyl-1,3-thiazole (2.7g, 0.017 moles) was stirred together without solvent at room temperature for 3h. The mixture was diluted with tetrahydrofuran (100ml) and then treated with tetrabutylammonium fluoride trihydrate (5.4g, 0.017 moles). After 1h the mixture was concentrated in vacuo and the residue partitioned between saturated potassium carbonate solution and chloroform. The organic layer was dried (Na2SO4) and evaporated to dryness. The residue was subjected to column chromatography on TLC alumina eluting with 0.5% methanol/chloroform. This gave an oil which was triturated with diethylether/methanol to yield the title compound (D33) as a buff solid (0.5g, 13%).

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