反応 #58794

反応方程式

compound ( 13 )

Allyl 1-Aminomethyl-1-Cyclohexane Acetate Hydrochloride

1-chloroethyl chloroformate

N-methylmorpholine

→

desired product ( 14 )

収率 100.5%

Allyl 1-{[(α-Chloroethoxy)carbonyl]aminomethyl}-1-Cyclohexane Acetate

収率 100.5%

溶媒

dichloromethane

diethyl ether

反応条件

後処理

1. 1
   温度while maintaining a temperature of less than 10° C
2. 2
   洗浄washed with water (100 mL) and brine (100 mL)
3. 3
   乾燥The organic phase was dried over anhydrous sodium sulfate
4. 4
   濃縮concentrated

実験手順

To a solution of compound (13) (30 g, 0.121 mol) in dichloromethane (100 mL) was slowly added 1-chloroethyl chloroformate (13 mL, 16.9 g, 0.119 mol). The reaction mixture was cooled to 0° C. and N-methylmorpholine (26.39 mL, 24.28 g, 0.24 mol) was slowly added over a period of 1 h while maintaining a temperature of less than 10° C. The resulting turbid solution was stirred for 30 min, and the reaction mixture was then diluted with diethyl ether (250 mL), washed with water (100 mL) and brine (100 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated to give the desired product (14) as light yellow viscous liquid (38 g, 99% yield). 1H NMR (CDCl3, 400 MHz): δ 1.35-1.58 (m, 10H), 1.78 (d, 3H), 2.32 (s, 2H), 3.22 (d, 2H), 4.57 (d, 2H), 5.25 (dd, 1H), 5.32 (dd, 1H), 5.52 (br. s, 1H), 5.90-5.94 (m, 1H), 6.54 (q, 1H).

出典