Реакция #58794

Уравнение реакции

compound ( 13 )

Allyl 1-Aminomethyl-1-Cyclohexane Acetate Hydrochloride

1-chloroethyl chloroformate

N-methylmorpholine

→

desired product ( 14 )

Выход 100.5%

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

Выход 100.5%

Растворители

dichloromethane

diethyl ether

Условия реакции

Обработка

1. 1
   Температураwhile maintaining a temperature of less than 10° C
2. 2
   Промывкаwashed with water (100 mL) and brine (100 mL)
3. 3
   СушкаThe organic phase was dried over anhydrous sodium sulfate
4. 4
   Концентрированиеconcentrated

Методика

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).

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