Triethylamine → HCID 53742937, compound

Participants

Reaction Steps

To a mixture of methyl isonipecotate (10.0 g, 69.8 mmol) and triethylamine (19.5 mL, 140 mmol) in tetrahydrofuran (200 mL) was added tert-butyl bromoacetate (10.3 mL, 69.8 mmol). The solution was heated at reflux for 24 h, concentrated under reduced pressure and purified via flash column chromatography (ethyl acetate:hexane, 10:90 to 100:0, methanol: dichloromethane, 1:99 to 5:95) to provide the title compound (18 g). 1H NMR (400 MHz, CDC3) δ 3.61 (s, 3H), 3.04 (s, 2H), 2.84 (d, J=11.5 Hz, 2H), 2.12-2.31 (m, 3H), 1.64-1.91 (m, 4H), 1.39 (s, 9H).

Provenance & Evidence