Neopentylamine → (+/-)-4-[1-(2,2-Dimethylpropyl-carbamoyl)-ethyl]-benzonitrile

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Reaction Steps

Add AlMe3 (1.72 mL, 3.44 mmol, 2M solution in hexane) to a solution of 2,2-dimethyl-propylamine (402 μL, 3.44 mmol) in DCM (0.5 mL) under nitrogen atmosphere. Stir the mixture for 15 min at room temperature and add ethyl 2-(4-cyanophenyl)propanoate. Heat the mixture at 40° C. overnight. Quench the reaction with 10N aqueous HCl and extract twice with DCM. Dry the combined organics extracts over Na2SO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (7:3) to obtain the desired intermediate (170 mg, 41%).

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