Triethylamine → HCID 43652195, compound

Participants

Reaction Steps

To an equimolar solution of 1-furan-2-yl-ethanone (250 mg, 2.27 mmol) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester (454 mg, 2.27 mmol) in dichloromethane (14 mL) 1M titanium(IV) chloride in dichloromethane (1.13 mL, 1.13 mmol) and triethylamine (0.31 mL, 2.27 mmol) were added. The reaction mixture was stirred under nitrogen atmosphere for 2 days. Then sodium cyanoborohydride (430 mg, 6.8 mmol) in methanol (7 mL) was added dropwise with stirring and the solution was allowed to stir overnight at room temperature. 35% sodium hydroxide was added and the product was extracted with ethyl acetate. The solvent was removed under reduce pressure and the crude was purified by flash chromatography (dichloromethane/methanol:95/5) to give the final compound as a red oil (406 mg, 61%).

Provenance & Evidence