Dichloromethane → n-{[(7s)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}-3-(7,8-dimethoxy-1,2,4,5-tetrahydro-3h-3-benzazepin-3-yl)-n-methyl-4-oxobutan-1-amine hydrochloride

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Reaction Steps

At ambient temperature, 2.53 g (12.2 mmol) of {[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}methylamine and 3.95 g (12.2 mmol/1 eq.) of the compound of Step 2 are mixed into 90 mL of dichloromethane. There are then added 3.88 g (18.3 mmol/1.5 eq.) of sodium triacetoxyborohydride and stirring is carried out at ambient temperature for 4 hours. There are then added 60 mL of 1N aqueous sodium hydroxide solution, followed by extraction twice with 150 mL of ethyl acetate. The combined organic phases are washed with 100 mL of water and then with 100 mL of saturated aqueous sodium chloride solution and are then dried over magnesium sulphate. After filtration and concentration, the residue is chromatographed over 300 g of silica (eluant:dichloromethane/ethanol/ammonia: 97/3/0.3) to yield the desired product in the form of the base. The latter is dissolved in 13 mL of isopropanol, converted into a salt using 0.67 mL of 4.8N ethanolic HCl and then recrystallised from 25 mL of ethyl acetate to yield the expected product.

Provenance & Evidence