Hydrogen Peroxide → HCID 178453573, compound

Participants

Reaction Steps

To a solution of {(R)-2-Hydroxy-1-methyl-1-[6-(trans-4-trifluoromethyl-cyclohexyloxy)-naphthalen-2-yl]-ethyl}-carbamic acid tert-butyl ester (172 mg, 0.000368 mol) and 1H-tetrazole (0.255 g, 0.00364 mol, ChemPacific) in tetrahydrofuran (3.00 mL, Acros) was added di-tert-butyl N,N-diethylphosphoramidite (512 μL, 0.00184 mol, Aldrich) and the reaction was stirred at rt for 16 hours. Hydrogen peroxide (250 μL, 0.0024 mol, Aldrich) was added and the reaction was stirred for 1.5 hours. The reaction was then quenched with 10% NaS2O3 in saturated sodium bicarbonate, extracted with EtOAc, washed with saturated sodium chloride and then dried with Na2SO4. The drying agent was filtered and the organic layer was concentrated in vacuo. The crude product was taken up in DCM and purified using silica gel chromatography (0-100% ethyl acetate in hexanes). Isolated was the product (Rf=0.52 in 1:1 hexanes/ethyl acetate) in 107.8 mg yield (44%).

Provenance & Evidence