Water → 4-(N-cyclohexylcarbonyl-N-(2-methyl-3-phenyl-2-(E)-propenyl)aminomethyl)-1-t-butoxycarbonylpiperidine

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Reaction Steps

To a solution of 4-(N-(2-methyl-3-phenyl-2-(E)-propenyl)aminomethyl)-1-t-butoxycarbonylpiperidine (1.44 g, 4.18 mmol) and triethylamine (0.80 g, 7.9 mmol) in dichloromethane (60 mL) stirring at 0° C. under argon, was added cyclohexanecarbonyl chloride (0.75 g, 5.1 mmol) in a single portion. After 5 min the mixture was allowed to warm to room temperature. Water (0.2 mL) was added, and the mixture was evaporated under vacuum. Column chromatography (loaded as a slurry in dichloromethane, silica gel, step-wise gradient of 10% to 38% ethyl acetate in hexane) provided 4-(N-cyclohexylcarbonyl-N-(2-methyl-3-phenyl-2-(E)-propenyl)aminomethyl)-1-t-butoxycarbonylpiperidine (1.67 g, 88% yield) as a colorless gum. TLC Rf=0.19, 25% ethyl acetate in hexane.

Provenance & Evidence