Tetrabutylammonium Fluoride → HCID 69544180, compound

Participants

Reaction Steps

To a solution of 3-t-butyldiphenylsilyloxy-1-{4-[(1S)-1-(t-butyldiphenylsilyloxymethyl)-3-methylbutylcarbamoyl]-1,3-thiazol-2-yl}azetidine (2.14 g, 3.72 mmol) (obtained as described in Reference Example 37(2)) in anhydrous tetrahydrofuran (107 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (8.94 ml, 8.94 mmol) in an ice bath. The mixture was stirred in the ice bath for 4 hours. 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 (9:1) as the eluant to afford 3-hydroxy-1-{4-[(1S)-1-(hydroxymethyl)-3-methyl-butylcarbamoyl]-1,3-thiazol-2-yl}azetidine (825 mg, yield 74%) as a pale yellow oil.

Provenance & Evidence