Triacetoxyperiodinane → (+/-)-Tert-butyl 1-(3-{[cyclopentyl(4-formylphenyl)acetyl]-amino}benzyl)cyclopropanecarboxylate

Participants

Reaction Steps

A solution of 4.0 g (8.63 mmol) of (+/−)-tert-butyl 1-[3-({cyclopentyl[4-(hydroxymethyl)phenyl]-acetyl}amino)benzyl]cyclopropanecarboxylate in 20 ml of dichloromethane was cooled to 0° C., and 4.39 g (10.35 mmol) of Dess-Martin reagent [1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one] were added. After the addition had ended, cooling was removed and the reaction mixture was stirred at RT for 3 h. The solution was then diluted with dichloromethane and washed successively with water, saturated sodium carbonate solution and saturated sodium chloride solution. The organic phase was dried with magnesium sulphate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 50:1→3:1). This gave 2.27 g of the target compound (53.2% of theory).

Provenance & Evidence