反応 #47771

反応方程式

aminoacetaldehyde diethyl acetal

CNBr

→

title compound

N-(2,2-Diethoxyethyl)carbodiimide

溶媒

ether

hexane

反応条件

後処理

1. 1
   その他The solid was removed by filtration
2. 2
   洗浄washed with ether
3. 3
   濃縮The combined filtrate was concentrated
4. 4
   その他Purification
5. 5
   洗浄by column chromatography (silica gel, eluting with dichloromethane to 4% methanol in dichloromethane, gradient)

実験手順

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).

出典