Facile ring opening of 2,3-epoxy-steroids with aromatic amines in ionic liquids

• Published in: Steroids Vol. 71; no. 8; pp. 706 - 711
• Main Authors: Horváth, Anita, Skoda-Földes, Rita, Mahó, Sándor, Berente, Zoltán, Kollár, László
• Format: Journal Article
• Language: English
• Published: NEW YORK Elsevier Inc 01.08.2006; Elsevier; Elsevier Science
• Subjects: 2,3-Epoxy derivatives; Amino Acids, Aromatic - chemistry; Amino Alcohols - chemical synthesis; Aminoalcohols; Aniline Compounds - chemistry; Biochemistry & Molecular Biology; Biological and medical sciences; Catalysis; Endocrinology & Metabolism; Fundamental and applied biological sciences. Psychology; Ionic liquids; Ions - chemistry; Ketosteroids - chemical synthesis; Ketosteroids - chemistry; Life Sciences & Biomedicine; Models, Biological; Molecular Conformation; Science & Technology; Solvents - chemistry; Steroids; Steroids, Heterocyclic - chemistry; Vertebrates: endocrinology; Ionic liquids; Aminoalcohols; 2,3-Epoxy derivatives; Steroids; ALCOHOLS; EPOXIDES; aminoalcohols; steroids; 2,3-epoxy derivatives; ionic liquids; EFFICIENT METHOD; Steroid; Steroids;2,3-Epoxy derivatives;Aminoalcohols;Ionic liquids
• ISSN: 0039-128X; 1878-5867
• DOI: 10.1016/j.steroids.2006.04.006

Efficient ring opening of steroidal 2,3-epoxides with stoichiometric amount of aromatic amines has been carried out using an ionic liquid ([bmim] +[BF 4] −) both as solvent and catalyst. The reactions were completely regio- and stereoselective in each case. The aminoalcohol products have chair conformations in ring A. The ionic liquid-mediated ring opening can efficiently be carried out with aliphatic amines like morpholine as well.