Reaktion #8676

ord-f28c838693d64d378a2dbf9cdb185727

Reaktionsgleichung

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

Edukte

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

Reagenzien

Keine

Lösungsmittel

Cc1ccccc1
toluene

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturunder reflux for 20 hours
  2. 2
    FiltrationThe precipitate is then filtered off with suction
  3. 3
    Waschenwashed with toluene
  4. 4
    EinengenThe combined toluene phases are concentrated in a rotary evaporator
  5. 5
    workup.DISTILLATIONdistilled in vacuo

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07091198B1uspto-grants-2006_08