1,1'-Carbonyldiimidazole → tert-butyl (2S)-2-((3R)-3-((3-chlorophenyl)(2-(ethylamino)-2-oxoethoxy)methyl)piperidine-1-carboxamido)-3-cyclohexylpropyl(methyl)carbamate

Participants

Reaction Steps

A solution of (S)-tert-butyl 2-amino-3-cyclohexylpropyl(methyl)carbamate (34.7 mg, 0.129 mmol) in CH2Cl2 (2 mL) was cooled in an ice-bath and CDI (25 mg, 1.2 mmol) and DIEA (83.2 mg, 0.11 mL, 0.645 mmol) were added. The mixture was stirred at rt for 0.5 h and 2-((3-chlorophenyl)((R)-piperidin-3-yl)methoxy)-N-ethylacetamide (40 mg, 0.129 mmol) was added. The reaction mixture was stirred overnight, washed with brine, dried over Na2SO4 and concentrated to give crude tert-butyl (2S)-2-((3R)-3-((3-chlorophenyl)(2-(ethylamino)-2-oxoethoxy)methyl)piperidine-1-carboxamido)-3-cyclohexylpropyl(methyl)carbamate (60 mg, yield: 75.6%). MS (E/Z): 607 (M+H+).

Provenance & Evidence