RSS-Feed abonnieren
DOI: 10.1055/s-2006-939036
Practical Synthesis of (S)-Pyrrolidin-2-yl-1H-tetrazole, Incorporating Efficient Protecting Group Removal by Flow-Reactor Hydrogenolysis
Publikationsverlauf
Publikationsdatum:
14. März 2006 (online)
Abstract
A practical, safe, high-yielding and efficient synthesis of (S)-pyrrolidin-2-yl-1H-tetrazole has been developed, which avoids the generation of ammonium azide in the cyclisation step and the use of a 9:1 acetic acid-water mixture as the solvent in the hydrogenation. The previously extended hydrogenolysis reaction time (three days) is now reduced to hours through the use of an H-CubeTM (a continuous-flow reactor employing a mixed hydrogen-liquid flow stream)
Key words
tetrazole - asymmetric - synthesis - organocatalysis - flow - hydrogenation
- 1
Cobb AJA.Shaw DM.Ley SV. Synlett 2004, 558 - 2
Cobb AJA.Shaw DM.Longbottom DA.Gold JB.Ley SV. Org. Biomol. Chem. 2005, 3: 84 - 3
Torii H.Nakadai M.Ishihara K.Saito S.Yamamoto H. Angew. Chem. Int. Ed. 2004, 43: 1983 - 4
Hartikka A.Arvidsson PI. Tetrahedron: Asymmetry 2004, 15: 1831 - 5
Cobb AJA.Longbottom DA.Shaw DM.Ley SV. Chem. Commun. 2004, 1808 - 6
Mitchell CET.Brenner SE.Ley SV. Chem. Commun. 2005, 5346 - 7
Ramachary DB.Barbas CF. Org. Lett. 2005, 7: 1577 - 8
Momiyama N.Torii H.Saito S.Yamamoto H. Proc. Natl. Acad. Sci. U.S.A. 2004, 101: 5374 - 9
Suri JT.Ramachary DB.Barbas CF. Org. Lett. 2005, 7: 1383 - 10
Thayumanavan NR.Tanaka F.Barbas CF. Org. Lett. 2004, 3541 - 11
Chowdari NS.Barbas CF. Org. Lett. 2005, 7: 867 - 12
Knudsen KR.Mitchell CET.Ley SV. Chem. Commun. 2006, 66 - 13
Kumarn S.Shaw DM.Longbottom DA.Ley SV. Org. Lett. 2005, 7: 4189 - 14
Marigo M.Jørgensen KA. Chem. Commun. 2006, in press - 15
Almquist RG.Chao WR.Jennings-White C. J. Med. Chem. 1985, 28: 1067 - 16
Hartikka A.Arvidsson PI. Eur. J. Org. Chem. 2005, 4287 - 17
Koguru K.Oga T.Mitsui S.Orita R. Synthesis 1998, 910 - 18
Saaby S.Knudsen KR.Ladlow M.Ley SV. Chem. Commun. 2005, 2909 - 19
Jones RV.Godorhazy L.Varga N.Szalay D.Urge L.Darvas F. J. Comb. Chem. 2006, 8: 110 - 20
Desai B.Kappe O. J. Comb. Chem. 2005, 7: 641
References and Notes
For further details, please refer to the product details on the company website: http://www.thalesnano.com. Address: Thales Nanotechnology, 1031 Budapest, Záhony ucta 7 (Graphisoft Park), Hungary. Fax: +36(1)6666190; Tel: +36(1)6666100.