Reaktion #58794

Reaktionsgleichung

compound ( 13 )

Allyl 1-Aminomethyl-1-Cyclohexane Acetate Hydrochloride

1-chloroethyl chloroformate

N-methylmorpholine

→

desired product ( 14 )

Ausbeute 100.5%

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

Ausbeute 100.5%

Lösungsmittel

dichloromethane

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwhile maintaining a temperature of less than 10° C
2. 2
   Waschenwashed with water (100 mL) and brine (100 mL)
3. 3
   TrocknenThe organic phase was dried over anhydrous sodium sulfate
4. 4
   Einengenconcentrated

Vorschrift

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).

Quelle