Ammonium formate → (S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamine

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A mixture of (S,S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-phenylethyl)amine (23 grams, 0.074 mole) and ammonium formate (30 grams, 0.48 mole) and 10% palladium on carbon (3.7 grams) in ethanol (300 ml) was heated under reflux for 2 hours. The mixture was filtered and the solvent was evaporated to give a residue which was partitioned between 5% sodium hydroxide and ether. Evaporation of the organic phase gave (S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamine as an oil (14 grams, 92%), M+ 205.

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