Tetrabutylammonium Fluoride → HCID 69544218, compound

Participants

Reaction Steps

To a solution of 3-t-butyldiphenylsilyloxy-1-{4-[(1S,2S)-1-(t-butyldiphenylsilyloxymethyl)-2-methylbutylcarbamoyl]-1,3-thiazol-2-yl}azetidine (1.89 g, 2.45 mmol) (obtained as described in Reference Example 38(2)) in anhydrous tetrahydrofuran (95 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (5.87 ml, 5.87 mmol) in an ice bath. The mixture was stirred in the ice bath overnight. 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,2S)-1-(hydroxymethyl)-2-methylbutylcarbamoyl]-1,3-thiazol-2-yl}azetidine (811 mg, yield 100%) as a pale yellow oil.

Provenance & Evidence