تفاعل #546705

معادلة التفاعل

sodium hydroxide

hydrogen peroxide

cis-N1,N2-Bis(benzyloxycarbonyl)-4-cyclohexene-1,2-diamine

borane

→

title compound

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

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONborane-dimethyl sulfide complex (7.4 ml) was added at 0° C.
2. 2
   workup.ADDITIONIce was added to the reaction mixture
3. 3
   workup.STIRRINGto stir the mixture for 1 hour
4. 4
   استخلاصThe reaction mixture was extracted with ethyl acetate
5. 5
   غسيلthe resultant organic layer was washed with saturated saline
6. 6
   تجفيفdried over anhydrous sodium sulfate
7. 7
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
8. 8
   أخرىthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=2:1)

الإجراء التجريبي

cis-N1,N2-Bis(benzyloxycarbonyl)-4-cyclohexene-1,2-diamine (10 g) was dissolved in absolute tetrahydrofuran (70 ml), borane-dimethyl sulfide complex (7.4 ml) was added at 0° C., and the mixture was gradually heated to room temperature and stirred for 14 hours. Ice was added to the reaction mixture to decompose excessive borane, and a 1N aqueous solution (80 ml) of sodium hydroxide and 30% aqueous hydrogen peroxide (80 ml) were added to stir the mixture for 1 hour. The reaction mixture was extracted with ethyl acetate, and the resultant organic layer was washed with saturated saline and 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=2:1) to obtain the title compound (9.2 g) as a colorless wax.

المصدر