Tetrabutylammonium Fluoride → HCID 22242865, compound

Participants

Reaction Steps

To a solution of 3-t-butyldiphenylsilyloxy-1-(4-{N-[2-(t-butyldiphenylsilyloxy)ethyl]-N-methyl-carbamoyl}-1,3-thiazol-2-yl)azetidine (2.24 g, 3.05 mmol) (obtained as described in Reference Example 40(2)) in anhydrous tetrahydrofuran (70 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (7.32 ml, 7.32 mmol) in an ice bath, and 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 ethyl acetate:methanol (20:1)→ethyl acetate:methanol (15:1) as the eluant to afford 3-hydroxy-1-{4-[N-(2-hydroxyethyl)-N-methyl-carbamoyl]-1,3-thiazol-2-yl}azetidine (833 mg, yield 94%) as a white solid.

Provenance & Evidence