Potassium Iodide → 3-(2-Methoxy-5-methylphenyl)-3-phenyl propanoic acid-(3-benzyl-3-azabicyclo[3.1.0]hexane-6-yl-carbamoyl)methyl ester

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Reaction Steps

The compound, 3-benzyl-3-azabicylo[3.1.0]hex-6-yl-2-chloroacetamide, 150 mg, 0.65 mmole, 1 eq (prepared by reacting 3-benzyl-3-azabicylo[3.1.0]hex-6-yl amine with 2-chloroacetyl chloride. The compound 3-benzyl-3-azabicyclo[3.1.0]hex-6-ylamine, in turn, can be prepared following the procedure of T. F. Braish et al., Synlett 1996, 1100) was dissolved in xylene. To the reaction mixture, potassium iodide was added with subsequent addition of (2-methoxy-5-methylphenyl)-3-phenyl propanoic acid (230 mg, 0.85 mmole, 1.5 eq) and 1,8-diazabicyclo[5.4.0]undec-7-ene. The reaction mixture was refluxed for 2 hours. Xylene was removed under pressure and the residue was dissolved in dichloromethane. The organic compound was then purified through column chromatography using 60% ethyl acetate in hexane.

Provenance & Evidence