Solvent-free Al(OTf)3-catalyzed aminolysis of 1,2-epoxides by 2-picolylamine: A key step in the synthesis of ionic liquids

Journal of Organic Chemistry

Volumn 69, Issue 22, 2004, Pages 7745-7747

  Fringuelli, Francesco ^a   Pizzo, Ferdinando ^a   Tortoioli, Simone ^a   Vaccaro, Luigi ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CATALYSIS; DERIVATIVES; ORGANIC SOLVENTS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

1,2-EPOXIDES; AMINOLYSIS REACTIONS; INTRAMOLECULAR CYCLIZATION; LEWIS ACID (LA);

AMINES;

1,2 EPOXIDE DERIVATIVE; 2 [(PYRIDIN 2' YL)METHYLAMINO]CYCLOHEXANOL; 2 PICOLYLAMINE; 5 [(4' METHYLPHENYL)SULFONYL] 1,2,3,4,4A,5,6,11A OCTAHYDROPYRIDO[1,2 A]QUINOXALIN 11 IUM METHANESULFONATE; ALUMINUM DERIVATIVE; AMINE; AMINOALCOHOL; CHLORINE DERIVATIVE; CYCLOHEXANE OXIDE; CYCLOHEXANOL DERIVATIVE; EPOXIDE; IONIC LIQUID; LEWIS ACID; MESYLIC ACID DERIVATIVE; N 2' PYRIDYLMETHYL DERIVATIVE; PYRIDINE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

AMINOLYSIS; ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; LIQUID; OPTICAL ROTATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REPRODUCIBILITY; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS; TECHNIQUE;

EID: 6344248974     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049335f     Document Type: Article

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27. 3 in DCM is not effective in these transformations.7c
28. 3 (∼5 min), 2.0 mmol (198 mg) of cyclohexene oxide (1a) was added and the reaction mixture warmed to 70 °C and left under vigorous magnetic stirring. After 3 h the reaction mixture was cooled to room temperature and the oily mixture was charged on a triethylamine-pretreated silica gel column Chromatograph and eluted with EtOAc/MeOH 95/5 solution. The β-amino alcohol 3a was isolated in 95% yield and recrystallizated from diethyl ether. For a full characterization chart see the Supporting Information.