Reacción #47771

Ecuación de reacción

aminoacetaldehyde diethyl acetal

CNBr

→

title compound

N-(2,2-Diethoxyethyl)carbodiimide

Disolventes

ether

hexane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solid was removed by filtration
2. 2
   Lavadowashed with ether
3. 3
   ConcentraciónThe combined filtrate was concentrated
4. 4
   OtroPurification
5. 5
   Lavadoby column chromatography (silica gel, eluting with dichloromethane to 4% methanol in dichloromethane, gradient)

Procedimiento

A solution of the aminoacetaldehyde diethyl acetal (13.16 g, 99 mmol) in ether (35 mL) was added to a suspension of CNBr (10.47 g, 99 mmol) in hexane (35 mL) at room temperature. The reaction mixture was stirred at room temperature overnight. The solid was removed by filtration and washed with ether. The combined filtrate was concentrated. Purification by column chromatography (silica gel, eluting with dichloromethane to 4% methanol in dichloromethane, gradient) afforded the title compound (7.0 g, 44.7%, one half of the starting amine served as a sacrificial base in the reaction) (Rf: 2.70, 4% methanol in dichloromethane, stain with 10% ethanolic molybdatophosphoric acid). 1H NMR 400 MHz (CDCl3) δ 4.58 (t, J=5.2 Hz, 1H), 3.77-3.69 (m, 2H), 3.65 (br, s, 1H), 3.60-352 (m, 2H), 3.16 (t, J=5.6 Hz, 1H), 1.23 (t, 6H, J=6.8 Hz).

Fuente