Hydrochloric Acid → tert-Butyl {4-[4-(hydroxymethyl)phenyl]-4-oxobutyl}methylcarbamate

Participants

Reaction Steps

[(4-Bromobenzyl)oxy](tert-butyl)dimethylsilane (2.30 g, 7.64 mmol), a compound described in the literature (Eur. J. Org. Chem.; EN, 8, 2001, 1549), was dissolved in tetrahydrofuran (7.6 mL), a 1.6 M n-butyllithium-hexane solution (4.37 mL, 7.00 mmol) was added at −78° C., and the mixture was stirred at the same temperature for 30 minutes. A solution of tert-butyl {4-[methoxy(methyl)amino]-4-oxobutyl}methylcarbamate (1.65 g, 6.36 mmol), a compound described in the literature (Bio. Org. Med. Chem. 2004, 12, 5147-5160), in tetrahydrofuran (7.6 mL) was further added at −78° C., and the temperature was increased to room temperature. After the reaction was completed, a 1 N tetrabutylammonium fluoride-tetrahydrofuran solution (12.7 mL, 12.7 mmol) was added. Subsequently, 1 N hydrochloric acid was further added. A saturated aqueous sodium hydrogencarbonate solution was further added, the mixture was extracted with ethyl acetate, and the resulting organic layer was dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (elution solvents, n-hexane:ethyl acetate=1:1→1:2, v/v) to give the title compound (1.29 g; yield, 48%) as a yellow oily substance.

Provenance & Evidence