Tetrabutylammonium Fluoride → 1-(4-Cyano-1,3-thiazol-2-yl)-3-hydroxyazetidine

Participants

Reaction Steps

To a solution of 3-t-butyldiphenylsilyloxy-1-(4-cyano-1,3-thiazol-2-yl)azetidine (2.36 g, 5.62 mmol) (obtained as described in Reference Example 4(1)) in anhydrous tetrahydrofuran (115 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (6.7 ml, 6.7 mmol) in an ice bath. The mixture was stirred in the ice bath 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 toluene:ethyl acetate (1:2) as the eluant to afford 1-(4-cyano-1,3-thiazol-2-yl)-3-hydroxyazetidine (0.78 g, yield 77%) as a white solid.

Provenance & Evidence