Hydrochloric Acid → 3-{1-[4-(4-Amino-3-chloro-5-trifluoromethyl-phenyl)-3-hydroxymethyl-butyryl]-piperidin-4-yl}1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one

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Reaction Steps

To a solution of 3.00 g (5.425 mmol) 2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-4-oxo-4-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-butyric acid (intermediate product 68) in 100 mL THF was added 1.054 g (6.500 mmol) CDl and the mixture was stirred for 2 hours at RT. This solution was added dropwise under a nitrogen atmosphere over 5 minutes to an ice-cooled solution of 0.728 g (19.250 mmol) sodium borohydride in 50 mL water and the mixture was stirred for 16 hours at RT. The reaction mixture was acidified with 1 N aqueous HCl to pH 2 and exhaustively extracted with EtOAc. The combined org. phases were washed with sat. aqueous NaCl solution, dried over sodium sulphate and evaporated i. vac.

Provenance & Evidence