Methyl 3-(tert-butylamino)propanoate synthesis

Yield:21539-55-9 77%

Reaction Conditions:

in methanol; for 96 h;Inert atmosphere;

Steps:

Methyl 3-(tert-Butylamino)propionate (16)

To a solution of tert-butyl amine (15) (34.8 g, 0.48 mol, 50 mL) in MeOH (380 mL) under N2 was added freshly distilled methyl acrylate (41.3 g, 0.48 mol, 43.2 mL). The resulting colorless solution was allowed to stand for 96 h under N2. The solvent was removed under reduced pressure. The crude product was collected by vacuum distillation at 82 °C/10 Torr (lit.15 bp 63 °C/10 Torr) to yield 58.5 g (77%) of (16) as a colorless liquid, which was used directly in the next step; 1H NMR 3.65 (s, 3H), 3.32 (s, 1H), 2.80 (m, 2H), 2.47 (m, 2H), 1.07 (s, 9H); IR 2950, 1749 cm-1

References:

Saulnier, Mark G.;Schreiber, Steven M.;Cavanaugh, Kerri L.;Perni, Robert B.;Joyner, H. Howard;Gribble, Gordon W. [Arkivoc,2020,vol. 2021,# 5,p. 15 - 23]