Diisopropylethylamine → tert-butyl (S)-2-(1-(3-((3-methoxypropoxy)(phenyl)methyl)piperidin-1-yl)-2-nitrovinylamino)-3-cyclohexylpropylcarbamate

Participants

Reaction Steps

3-((3-Methoxypropoxy)(phenyl)methyl)piperidine hydrochloride (177 mg, 0.59 mmol), 1,1-bis(methylthio)-2-nitroethene (117 mg, 0.71 mmol, 1.2 equiv), and diisopropylethylamine (500 μL, 2.8 mmol, 5 equiv) were dissolved in acetonitrile (5 mL) and put on a shaker for 2 h. LC-MS indicated the presence of 3-((3-methoxypropoxy)(phenyl)methyl)-1-((Z)-1-(methylthio)-2-nitrovinyl)piperidine. Tert-butyl (S)-2-amino-3-cyclohexylpropylcarbamate (˜300 mg, 1.17 mmol, 2 equiv) was added to the mixture and shaking was continued overnight. The mixture was concentrated and purified by prep HPLC to afford tert-butyl (S)-2-(1-(3-((3-methoxypropoxy)(phenyl)methyl)piperidin-1-yl)-2-nitrovinylamino)-3-cyclohexylpropylcarbamate (22 mg, 6.6%). LC-MS (3 min) tR=1.92 min. m/z 589 (M+1).

Provenance & Evidence