Benzylamine → 3-Benzyl-8-oxa-3-azabicyclo[3.2.1]octane

HRID 8580Notes

Reaction equation

HRID 8580 reaction equation
CC1C=CC(S(O[CH2:12][CH:13]2[O:17][CH:16]([CH2:18]OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:15][CH2:14]2)(=O)=O)=CC=1.[CH2:30]([NH2:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1(C)C=CC=CC=1>[CH2:30]([N:37]1[CH2:12][CH:13]2[O:17][CH:16]([CH2:15][CH2:14]2)[CH2:18]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 259634(Tetrahydrofuran-2,5-diyl)bis(methylene) bis(4-methylbenzenesulfonate)

Product 1

HCID 120692303-Benzyl-8-oxa-3-azabicyclo[3.2.1]octane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  1. temperatureunder reflux for 20 hours
  2. filtrationThe precipitate is then filtered off with suction
  3. washwashed with toluene
  4. concentrationThe combined toluene phases are concentrated in a rotary evaporator
  5. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-f28c838693d64d378a2dbf9cdb185727
Source dataset
uspto-grants-2006_08
Patent number
US07091198B1

Reaction notes

Loading…