(1S)-1-(furan-2-yl)ethanamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (1S)-1-(Furan-2-yl)ethanamine (0.55 gr, 5 mmol) and 1-cyclohexylpiperidin-4-one (0.91 gr, 5 mmol) were dissolved in dry dichloromethane (20 mL) in the presence of triethylamine (2 mL, 15 mmol) and titanium(IV) chloride (1M in dichloromethane, 2.5 mmol, 2.5 mL). Reaction mixture was stirred under nitrogen atmosphere for 16 hours. After dilution with methanol (10 mL), sodium cyanoborohydride was added (0.95 gr, 25 mmol) and the resulting reaction mixture was stirred for 4 hours. After dilution with ethyl acetate, the organic phase was washed with 15% ammonium hydroxide and evaporated to dryness. Title compound (0.72 gr, Y=52%) was isolated by column chromatography (dichloromethane/methanol/7N ammonia in methanol 96:2:2) Reaction mixture the resulting reaction mixture was stirred for 4 hours After dilution with ethyl acetate, the organic phase was washed with 15% ammonium hydroxide evaporated to dryness