ethyl 3-(furan-2-ylmethylamino)propanoate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Ethyl 3-[(furan-2-ylmethyl)amino]propionate (10.8 g) prepared in the step 2 and 18.3 mL of triethylamine were dissolved in 180 mL of methylene chloride, 7.14 g of ethyl chloroformate was added by slowly dropping thereinto under cooling with ice and the mixture was stirred at room temperature for 5 hours. Water (200 mL) was added to the reaction solution and the mixture was subjected to extraction with methylene chloride. The organic layer was washed with water and a saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate and the solvent was evaporated in vacuo therefrom. The residue was purified by silica gel column chromatography to give 13.77 g of the objective compound as yellow liquid. under cooling with ice the mixture was subjected to extraction with methylene chloride The organic layer was washed with water a saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate the solvent was evaporated in vacuo The residue was purified by silica gel column chromatography

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

Procedure: Ethyl 3-[(furan-2-ylmethylene)amino]propionate (19.2 g) prepared in the step 1 was dissolved in 200 mL of dry ethanol, 4.46 g of sodium borohydride was slowly added thereto little by little at room temperature and the mixture was stirred overnight at room temperature. The solvent was evaporated in vacuo from the reaction and the residue was poured over 300 mL of 10% aqueous solution of acetic acid. The resulting aqueous solution was washed with diethyl ether, neutralized with 10% aqueous ammonia and subjected to extraction with diethyl ether. The organic layer was washed with water and a saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate and the solvent was evaporated in vacuo therefrom to give 10.8 g of the objective compound as yellow liquid. The solvent was evaporated in vacuo from the reaction the residue was poured over 300 mL of 10% aqueous solution of acetic acid The resulting aqueous solution was washed with diethyl ether subjected to extraction with diethyl ether The organic layer was washed with water a saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate the solvent was evaporated in vacuo