Acetic Acid → HCID 22243002, compound

Participants

Reaction Steps

To a solution of 4-t-butyldimethylsilyloxy-1-(4-p-nitrobenzyloxycarbonyl-1,3-thiazol-2-yl)piperidine (300 mg, 0.628 mmol) (obtained as described in Reference Example 14(3)) in anhydrous tetrahydrofuran (15 ml) were added acetic acid (0.22 ml, 0.628 mmol) and a solution of 1M tetrabutylammonium fluoride in tetrahydrofuran (3.76 ml, 3.76 mmol) in an ice bath, and the mixture was then stirred at room temperature for 21 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by chromatography on a silica gel column using ethyl acetate:methanol (10:1) as the eluant to afford 1-(4-p-nitrobenzyloxycarbonyl-1,3-thiazol-2-yl)-4-hydroxypiperidine (123 mg, yield 54%) as a pale yellow solid.

Provenance & Evidence