تفاعل #633649

معادلة التفاعل

triethylamine

Dimethylsulfoxide

oxalyl chloride

(1R*,2S*)-N1,N2-bis(benzyloxycarbonyl)-4-hydroxy-1,2-cyclohexanediamine

→

title compound

المردود 87.4%

(±)-cis-N1,N2-Bis(benzyloxycarbonyl)-4-oxo-1,2-cyclohexanediamine

المردود 87.4%

المذيبات

dichloromethane

water

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was heated to room temperature as it
2. 2
   استخلاصextracted with methylene chloride
3. 3
   غسيلThe resultant organic layer was washed with saturated saline
4. 4
   تجفيفdried over anhydrous sodium sulfate
5. 5
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
6. 6
   أخرىthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:1)

الإجراء التجريبي

Dimethylsulfoxide (8.2 ml) was added to a solution of oxalyl chloride (9.9 ml) in dichloromethane (90 ml) at −60° C., and a solution of (1R*,2S*)-N1,N2-bis(benzyloxycarbonyl)-4-hydroxy-1,2-cyclohexanediamine (9.2 g) in tetrahydrofuran (90 ml) was added to the mixture in one portion. After 1 hour, the temperature of the mixture was raised to −40° C., and triethylamine (26 ml) was added in one portion. The mixture was heated to room temperature as it is, and stirred for 3 hours. The reaction mixture was poured into water and extracted with methylene chloride. The resultant organic layer was washed with saturated saline and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:1) to obtain the title compound (8.0 g) as a pale yellow solid.

المصدر