methyl 2-(propylamino)acetate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of glycine methyl ester HCl (5.0 g, 39.8 mmol) in acetonitrile (100 mL) was treated with propyl bromide (3.7 mL, 39.8 mmol), and diisopropylethylamine (13.9 mL, 79.6 mmol). After stirring at room temperature for 1 hour, the mixture was heated at reflux overnight. Solution occurred at reflux temperature. The solvent was removed under reduced pressure and the residue triturated with Et2O/EtOAc. Filtering and removal of the solvent under pressure left 1.13 g of the crude product. Chromatography on silica gel, eluting with CHCl3/MeOH (98:2) gave 0.53 g (10.2% yield) of the product as a yellow oil. the mixture was heated at reflux overnight at reflux temperature The solvent was removed under reduced pressure the residue triturated with Et2O/EtOAc Filtering removal of the solvent under pressure left 1.13 g of the crude product Chromatography on silica gel, eluting with CHCl3/MeOH (98:2)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of glycine methyl ester HCl (5.0 g, 39.8 mmol) in acetonitrile (100 mL) was treated with propyl bromide (3.7 mL, 39.8 mmol), and diisopropylethylamine (13.9 mL, 79.6 mmol). After stirring at room temperature for 1 hour, the mixture was heated at reflux overnight. Solution occurred at reflux temperature. The solvent was removed under reduced pressure and the residue triturated with Et2O/EtOAc. Filtering and removal of the solvent under pressure left 1.13 g of the crude product. Chromatography on silica gel, eluting with CHCl3/MeOH (98:2) gave 0.53 g (10.2% yield) of the product as a yellow oil. the mixture was heated at reflux overnight at reflux temperature The solvent was removed under reduced pressure the residue triturated with Et2O/EtOAc Filtering removal of the solvent under pressure left 1.13 g of the crude product Chromatography on silica gel, eluting with CHCl3/MeOH (98:2)