Reacción #58791

Ecuación de reacción

compound ( 6 )

Benzyl 1-Aminomethyl-1-Cyclohexane Acetate Hydrochloride

1-chloroethyl chloroformate

N-methylmorpholine

→

title compound ( 9 )

Rendimiento 100.6%

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

Rendimiento 100.6%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawith cooling, over a one hour period
2. 2
   workup.STIRRINGThe resulting turbid solution was stirred for 30 min
3. 3
   Otrothe reaction
4. 4
   LavadoThe reaction mixture was washed with water (2×2 L) and brine (1 L)
5. 5
   Secadodried over sodium sulfate
6. 6
   OtroEvaporation of the solvent

Procedimiento

In a 5-liter, 3-neck, round bottom flask, stirred mechanically and under nitrogen, was added dichloromethane (1.5 L), compound (6) (1.85 mol) and 1-chloroethyl chloroformate (258 g, 1.81 mol). The resulting solution was cooled to 15° C. and N-methylmorpholine (396 mL, 3.60 mol) was added slowly, with cooling, over a one hour period. The resulting turbid solution was stirred for 30 min, after which 1H—NMR analysis showed the reaction to be complete. The reaction mixture was washed with water (2×2 L) and brine (1 L) and dried over sodium sulfate. Evaporation of the solvent afforded the title compound (9) as an orange oil (670 g, 98% yield). 1HNMR (CDCl3, 400 MHz): 1.33-1.53 (m, 10H), 1.75 (d, 3H), 2.33 (s, 2H), 3.18 (d, 2H), 5.09 (s, 2H), 5.58 (t, 1H), 6.53 (q, 1H), 7.29-7.33 (m, 5H).

Fuente