Reaktion #82991

Reaktionsgleichung

3-benzyl-3-azabicyclo[3.1.0]hexane-6-carboxylic acid

ethyl 3-benzyl-3-azabicyclo[3.1.0]hexane-6-carboxylate

NaOH

triethylamine

DPPA

→

3-benzyl-6-t-butoxycarbonylamino-3-azabicyclo[3.1.0]hexane

Ausbeute 31.0%

Lösungsmittel

water

t-butanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeobtained
2. 2
   Temperaturunder reflux in a nitrogen atmosphere for 19 hours
3. 3
   Temperaturby cooling the reaction mixture
4. 4
   Extraktionextracting with toluene
5. 5
   Waschenwashing the organic layer successively with an aqueous solution of Na2CO3, water
6. 6
   Trocknena saturated aqueous solution of NaCl, drying over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONdistilling off the solvent under reduced pressure
8. 8
   Sonstigepurifying the residue

Vorschrift

A mixture of 3-benzyl-3-azabicyclo[3.1.0]hexane-6-carboxylic acid (116 mg, 0.53 mmol) obtained by treating ethyl 3-benzyl-3-azabicyclo[3.1.0]hexane-6-carboxylate obtained in step 5 of Example 1, with an aqueous solution of NaOH, with triethylamine (239 mg, 2.36 mmol), DPPA (303 mg, 1.10 mmol) and t-butanol (4 ml), was heated under reflux in a nitrogen atmosphere for 19 hours, followed by cooling the reaction mixture, pouring it into water, extracting with toluene, washing the organic layer successively with an aqueous solution of Na2CO3, water and a saturated aqueous solution of NaCl, drying over anhydrous magnesium sulfate, distilling off the solvent under reduced pressure and purifying the residue according to thin-layer chromatography (developing solvent: chloroform:methanol=20:1), to obtain 3-benzyl-6-t-butoxycarbonylamino-3-azabicyclo[3.1.0]hexane (47 mg, 0.16 mmol, 31%).

Quelle