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

Participants

Reaction Steps

To a solution of 3-t-butyldiphenylsilyloxy-1-(4-hydroxymethyl-1,3-thiazol-2-yl)azetidine (548.5 mg, 1.29 mmol) (obtained as described in Reference Example 2(2)) in anhydrous tetrahydrofuran (28 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (1.56 ml, 1.56 mmol) in an ice bath, and the mixture was then 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 ethyl acetate:methanol (10:1) as the eluant to afford 1-(4-hydroxymethyl-1,3-thiazol-2-yl)-3-hydroxyazetidine (230 mg, yield 96%) as a white solid.

Provenance & Evidence