Reacción #8676

ord-f28c838693d64d378a2dbf9cdb185727

Ecuación de reacción

Cc1ccc(S(=O)(=O)OCC2CCC(COS(=O)(=O)c3ccc(C)cc3)O2)cc1
2,5-anhydro-3,4-dideoxy-1,6-bis-O-[(4-methylphenyl)sulfonyl]-hexitol
Cc1ccc(S(=O)(=O)OCC2CCC(COS(=O)(=O)c3ccc(C)cc3)O2)cc1
2,5-Anhydro-3,4-dideoxy-1,6-bis-O-[(4-methylphenyl)sulfonyl]hexitol
NCc1ccccc1
benzylamine
→
c1ccc(CN2CC3CCC(C2)O3)cc1
benzylamine
c1ccc(CN2CC3CCC(C2)O3)cc1
3-Benzyl-8-oxa-3-azabicyclo[3.2.1]octane

Reactantes

Cc1ccc(S(=O)(=O)OCC2CCC(COS(=O)(=O)c3ccc(C)cc3)O2)cc1
2,5-anhydro-3,4-dideoxy-1,6-bis-O-[(4-methylphenyl)sulfonyl]-hexitol
Cc1ccc(S(=O)(=O)OCC2CCC(COS(=O)(=O)c3ccc(C)cc3)O2)cc1
2,5-Anhydro-3,4-dideoxy-1,6-bis-O-[(4-methylphenyl)sulfonyl]hexitol
NCc1ccccc1
benzylamine

Reactivos

Ninguno

Disolventes

Cc1ccccc1
toluene

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturaunder reflux for 20 hours
  2. 2
    FiltraciónThe precipitate is then filtered off with suction
  3. 3
    Lavadowashed with toluene
  4. 4
    ConcentraciónThe combined toluene phases are concentrated in a rotary evaporator
  5. 5
    workup.DISTILLATIONdistilled in vacuo

Procedimiento

112 g (250 mmol) of 2,5-anhydro-3,4-dideoxy-1,6-bis-O-[(4-methylphenyl)sulfonyl]-hexitol from step 1 and 90.7 g (840 mmol) of benzylamine in 500 ml of toluene are heated under reflux for 20 hours. The precipitate is then filtered off with suction and washed with toluene. The combined toluene phases are concentrated in a rotary evaporator and distilled in vacuo. After a benzylamine fore-run, the product is obtained.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07091198B1uspto-grants-2006_08