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

Participants

Reaction Steps

To a solution of 3-t-butyldiphenylsilyloxy-1-(4-carbamoyl-1,3-thiazol-2-yl)azetidine (6.7 g, 15.3 mmol) (obtained as described in Reference Example 3(1)) in anhydrous tetrahydrofuran (200 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (18.4 ml) in an ice bath. The mixture was stirred 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→10% methanol in ethyl acetate as the eluant to afford 1-(4-carbamoyl-1,3-thiazol-2-yl)-3-hydroxyazetidine (2.78 g, yield 91%) as a pale yellow solid.

Provenance & Evidence