Acetic Acid → N-{[(7S)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-methyl}cyclopentanamine

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Reaction Steps

At ambient temperature, 2.9 g (15 mmol) of {[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}amine and 1.3 mL (15 mmol/1 eq.) of cyclopentanone are mixed into 60 mL of dichloromethane. There are then added 4.8 g (22.5 mmol/1.5 eq.) of sodium triacetoxyborohydride and then 0.86 mL (15 mmol/1 eq.) of acetic acid, and stirring is carried out at ambient temperature for 4 hours. 90 mL of 1N sodium hydroxide solution are then poured in; extraction with two 120 mL quantities of ether is then carried out. The combined organic phases are washed with 90 mL of water and then with 90 mL of saturated aqueous sodium chloride solution and are then dried over magnesium sulphate. After filtration and concentration, the desired product is collected.

Provenance & Evidence