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Synthesis 2007(24): 3787-3790
DOI: 10.1055/s-2007-990902
DOI: 10.1055/s-2007-990902
PAPER
© Georg Thieme Verlag Stuttgart · New YorkFacile Synthesis of 11-Hydroxy-2-methoxyaporphine: A Potential Dopamine D1 Receptor Ligand
Further Information
Received
24 May 2007
Publication Date:
15 November 2007 (online)
Publication History
Publication Date:
15 November 2007 (online)

Abstract
11-Hydroxy-2-methoxyaporphine was synthesized from oripavine in three steps with an overall yield of 37.8%. The key step involved the palladium on carbon catalyzed reduction of 11-hydroxy-2-methoxy-10-O-[(trifluoromethyl)sulfonyl]aporphine using magnesium metal in methanol at room temperature in the presence of ammonium acetate.
Key words
aporphine - synthesis - rearrangement - reduction - deoxygenation
- 1a
Zhang A.Zhang Y.Branfman AR.Baldessarini RJ.Neumeyer JL. J. Med. Chem. 2007, 50: 171 - 1b
Zhang A.Neumeyer JL.Baldessarini RJ. Chem. Rev. 2007, 107: 274 - 2a
Gao YG.Baldessarini RJ.Kula NS.Neumeyer JL. J. Med. Chem. 1990, 33: 1800 - 2b
Ramsby S.Neumeyer JL.Grigoriadis D.Seeman P. J. Med. Chem. 1989, 32: 1198 - 2c
Baldessarini RJ.Kula NS.Gao Y.Campbell A.Neumeyer JL. Neuropharmacology 1991, 30: 97 - 2d
Søndergaard K.Kristensen JL.Palner M.Gillings N.Knudsen GM.Roth BL.Begtrup M. Org. Biomol. Chem. 2005, 3: 4077 - 3a
Csutoras C.Zhang A.Zhang K.Kula NS.Baldessarini RJ.Neumeyer JL. Bioorg. Med. Chem. 2004, 12: 3553 - 3b
Neumeyer JL.Granchelli FE.Fuxe K.Ungerstedt U.Corrodi H. J. Med. Chem. 1974, 17: 1090 - 3c
Neumeyer JL.Arana GW.Law SJ.Lamont JS.Kula NS.Baldessarini RJ. J. Med. Chem. 1981, 24: 1440 - 3d
Ram VJ.Neumeyer JL. J. Org. Chem. 1982, 47: 4372 - 3e
Zhang A.Csutoras C.Zong R.Neumeyer JL. Org. Lett. 2005, 7: 3239 - 4
Lin Z,Francis CA,Kaldahl CA,Antczak KG, andKumar V. inventors; US 6790959. ; Chem. Abstr. 2004, 141, 277800MissingFormLabel - 5a
Mudryk B,Sapino C,Dung J.-S, andSebastian A. inventors; US 6090943. ; Chem. Abstr. 1999, 130, 110451 - 5b
Coop A.Rice KC. Heterocycles 1998, 49: 43 - 6
Huang B.-S,Lu Y,Ji B.-Y, andChristodoulou AP. inventors; WO 9902529. ; Chem. Abstr. 1999, 130, 125256MissingFormLabel - 7
Rapoport H.Barber RB. J. Med. Chem. 1975, 18: 1074 - 8a
Coop A.Lewis JW.Rice KC. J. Org. Chem. 1996, 61: 6774 - 8b
Coop A.Janetka JW.Lewis JW.Rice KC. J. Org. Chem. 1998, 63: 4392 - 9a
Cacchi S.Ciattini PG.Morera E.Ortar G. Tetrahedron Lett. 1986, 27: 5541 - 9b
Chen Q.-Y.He Y.-B.Yang Z.-Y. J. Chem. Soc., Chem. Commun. 1986, 1452 - 9c
Cabri W.De Bernardinis S.Francalanci F.Penco S. J. Org. Chem. 1990, 55: 350 - 9d
Saa JM.Dopico M.Martorell G.Garcia-Raso A. J. Org. Chem. 1990, 55: 991 - 10
Sajiki H.Mori A.Mizusaki T.Ikawa T.Maegawa T.Hirota K. Org. Lett. 2006, 8: 987 - 11
Kula NS.Baldessarini RJ.Kebabian JW.Bakthavachalam V.Xu L. Eur. J. Pharmacol. 1997, 331: 333