Hydrazine hydrate (1:1) → (+/-)-Tert-butyl 3-[3-({[4-(aminomethyl)phenyl](cyclopentyl)acetyl}amino)-2-methylphenyl]propanoate

Participants

Reaction Steps

8.5 g (14.6 mmol) of tert-butyl(+/−)-3-(3-(2-cyclopentyl-2-(4-((1,3-dioxoisoindolin-2-yl)methyl)phenyl)acetamido)-2-methylphenyl)propanoate were initially charged in 85 ml of ethanol, and 2.35 ml (48.3 mmol) of hydrazine hydrate were added. The reaction mixture was heated under reflux overnight. After cooling to room temperature, the precipitated solid was filtered off and washed with ethanol. The filtrate was concentrated, the residue was triturated with acetonitrile and the precipitated crystals were filtered off with suction and discarded. The mother liquor was concentrated and the residue was purified by flash chromatography on silica gel (mobile phase dichloromethane/methanol/aq. ammonia 100:5:1). This gave 4.51 g (68% of theory) of the target compound.

Provenance & Evidence