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A Novel Synthesis of (4aS,7aS)-Octahydro-1H-pyrrolo[3,4-b]pyridine: An Intermediate of Moxifloxacin Hydrochloride
Corresponding Author(s) : Rakeshwar Bandichhor
Asian Journal of Chemistry,
Vol. 25 No. 15 (2013): Vol 25 Issue 15
Abstract
A novel synthesis of (4aS, 7aS)-octahydro-1H-pyrrolo[3,4-b]pyridine (1) is demonstrated alongwith recovery and reuse of chiral auxiliary naproxen. Further to this alternative stereoselective reduction procedures on 6-benzyl-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione 3 enabling the desired chirality in the nonane 1 is demonstrated.
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- U. Petersen, T. Schenke, A. Krebs, K. Grohe, M. Schriewer, I. Haller, K. Metzger, R. Endermann and H. Zeiler, EP 0,350,733 (1990).
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- W. Tianjun, Faming Zhuanli Shenqing, 7 (2010).
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- (a) F. Peter, WO58, 532, 1999; (b) D. Claus, Ger.Offen. WO 09, 200, 1999; (c) F. Peter, US Patent 6, 235, 908 (2001); (d) D. Herbert, K. Andreas, L. Walter, P. Hanns-Ingolf, S. Dietrich, G. Rolf and R. Tobias, US Patent 0,044,205 (2004); (e) L. Mingliang, W. Yonggang, S. Lanying and G. Huiyuan, Zhongguo Yiyao Gongye Zazhi, 35, 129 (2004); (f) P. Xianhua, T. He, O. Wenhua, R. Libo and Y. Wenqiu, Faming Zhuanli Shenqing, 13 (2009); (g) M. Riccardo, A. Glancarlo, B. Elisabetta, C. Andrea, F. Stefano and G. Marco, WO100,215 (2010).
- J.S. Grimm, C.A. Maryanoff, M. Patel, D.C. Palmer, K.L. Sorgi, S. Stefanick, R.R.H. Webster and X. Zhang, Org. Process Res. Dev., 6, 938 (2002).
- M.S. Sakya, D.V.M. Berg, K. Pouwer, M.J. Humphrey, J.C. Helal and J.C. O’Donnel, Tetrahedron Lett., 51, 5859 (2010)
References
U. Petersen, T. Schenke, A. Krebs, K. Grohe, M. Schriewer, I. Haller, K. Metzger, R. Endermann and H. Zeiler, EP 0,350,733 (1990).
U. Petersen, A. Krebs, T. Schenke, T. Philipps, K. Grohe, K.D. Bremm, R. Endermann, K.G. Metzger and I. Haller, EP0, 550, 903 (1992).
A. Ramakrishnan and S.B. Narayan, V. WO 125,425 (2009).
J.W. Kim, H.T. Park, H.M. Kim, J.B. Kim and D.N. Pearson, US Patent 5,770,597 (1998).
(a) W. Zheqing, F. Shushan and C. Yongzhi, WO085480 (2008); (b) Z. Wang, S. Feng and Y. Cheng, US Patent 0,221,329 (2008).
W. Tianjun, Faming Zhuanli Shenqing, 7 (2010).
O. Masatoshi and N. Akira, WO 122,774 (2010).
(a) F. Peter, WO58, 532, 1999; (b) D. Claus, Ger.Offen. WO 09, 200, 1999; (c) F. Peter, US Patent 6, 235, 908 (2001); (d) D. Herbert, K. Andreas, L. Walter, P. Hanns-Ingolf, S. Dietrich, G. Rolf and R. Tobias, US Patent 0,044,205 (2004); (e) L. Mingliang, W. Yonggang, S. Lanying and G. Huiyuan, Zhongguo Yiyao Gongye Zazhi, 35, 129 (2004); (f) P. Xianhua, T. He, O. Wenhua, R. Libo and Y. Wenqiu, Faming Zhuanli Shenqing, 13 (2009); (g) M. Riccardo, A. Glancarlo, B. Elisabetta, C. Andrea, F. Stefano and G. Marco, WO100,215 (2010).
J.S. Grimm, C.A. Maryanoff, M. Patel, D.C. Palmer, K.L. Sorgi, S. Stefanick, R.R.H. Webster and X. Zhang, Org. Process Res. Dev., 6, 938 (2002).
M.S. Sakya, D.V.M. Berg, K. Pouwer, M.J. Humphrey, J.C. Helal and J.C. O’Donnel, Tetrahedron Lett., 51, 5859 (2010)