Tetrahydro-2,5-dimethoxyfuran-3-carbaldehyde → trans-[2-(3-Formyl-pyrrol-1-yl)-cyclohexyl]-carbamic acid tert-butyl ester

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Reaction Steps

A solution of trans-(2-amino-cyclohexyl)-carbamic acid tert-butyl ester (Tetrahedron Lett. 2000, 41, 9607; 400 mg, 1.87 mmol) and 2,5-dimethoxy-3-tetrahydrofurancarboxaldehyde (365 mg, 2.05 mmol) in pyridine (0.5 mL) and acetic acid (0.82 mL) was heated at 100° C. for 4.5 h. After cooling, the reaction mixture was partitioned between ethyl acetate and 10% aq. citric acid solution. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane-ethyl acetate gradient) yielded the title compound (334 mg, 61%). Off-white solid, MS (ISP) 293.3 (M+H)+.

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