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

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Reaction Steps

To a solution of 3-t-butyldiphenylsilyloxy-1-(4-pyrrolidinocarbonyl-1,3-thiazol-2-yl)azetidine (775 mg, 1.58 mmol) (obtained as described in Reference Example 26(1)) in anhydrous tetrahydrofuran (30 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (2.01 ml, 2.01 mmol) in an ice bath, and then 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 (20:1) as the eluant to afford 3-hydroxy-1-(4-pyrrolidinocarbonyl-1,3-thiazol-2-yl)azetidine (290 mg, yield 72%) as a white solid.

Provenance & Evidence