Diisopropylethylamine → HCID 54391593, compound

Participants

Reaction Steps

To a solution of piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (275 mg, 1.2 mmol) in CH2Cl2 (2 ml) was added diisopropylethylamine (0.23 ml, 1.32 mmol). The resulting solution was stirred for 5 minutes then TBTU (337 mg, 1.26 mmol) was added and stirred for 20 minutes. To the reaction mixture was added a solution of 4-(2-aminomethyl-pyridin-4-yl)-benzoic acid methyl ester trifluoroacetic acid salt (356 mg, 1 mmol, reference example 103a) and diisopropylethylamine (0.192 ml, 1.1 mmol) in CH2Cl2 (2 ml). The reaction mixture was stirred 45 minutes then concentrated under reduced pressure. The residue was purified by flash chromatography (eluting with 40% ethyl acetate/10% methanol/hexanes) to give 455 mg of product as a white foam. MS (ion spray) m/z 454 (M+H)+.

Provenance & Evidence