Sodium Hydroxide → HCID 86644628, compound

Participants

Reaction Steps

To a mixture of benzyl [(1S,2S)-2-hydroxycyclopentyl]carbamate (1.3 g) and benzene (13 ml) were added, tert-butyl bromoacetate (3.2 g), hydrogen tetrabutyl ammonium sulfate (0.46 g), and a 50% aqueous NaOH solution (13 ml) under ice-cooling, followed by stirring under ice-cooling for 1 hour and further at room temperature for 2 hours. The reaction mixture was poured into ice-water, extracted with ethyl acetate, then washed with water and saturated brine in this order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1→7:1→5:1) to obtain tert-butyl {[(1S,2S)-2-{[(benzyloxy)carbonyl]amino}cyclopentyl]oxy}acetate (1.3 g).

Provenance & Evidence