Tetrabutylammonium Fluoride → 3-Hydroxy-1-(4-piperidinocarbonyl-1,3-thiazol-2-yl)azetidine

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Reaction Steps

To a solution of 3-t-butyldiphenylsilyloxy-1-(4-piperidinocarbonyl-1,3-thiazol-2-yl)azetidine (607 mg, 1.20 mmol) (obtained as described in Reference Example 27(1)) in anhydrous tetrahydrofuran (25 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (1.40 ml, 1.40 mmol) in an ice bath, and the mixture was stirred at room temperature for 1 hour. After checking the completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate→ethyl acetate:methanol (9:1) as the eluant to afford 3-hydroxy-1-(4-piperidinocarbonyl-1,3-thiazol-2-yl)azetidine (310 mg, yield 97%) as a white solid.

Provenance & Evidence