Graphical Synthetic Routes of (S,S)-Reboxetine

HAN Shilei1, ZHAO Shiming2*, LUO Zhenfu2, WU Xuedan2, CHENG Jinbo3

主办:上海医药工业研究院
   中国药学会
   中国化学制药工业协会
ISSN 1001-8255   CN 31-1243/R   ZYGZEA
Chinese Journal of Pharmaceuticals ›› 2013, Vol. 44 ›› Issue (10) : 1061-1064.

Graphical Synthetic Routes of (S,S)-Reboxetine

Author information +
History +

Cite this article

Download Citations
HAN Shilei1, ZHAO Shiming2*, LUO Zhenfu2, WU Xuedan2, CHENG Jinbo3. Graphical Synthetic Routes of (S,S)-Reboxetine. Chinese Journal of Pharmaceuticals. 2013, 44(10): 1061-1064

References

[1] Burrow GD, Magure KP, Norman TR. Antidepressant efficacy and tolerability of the selective norepinephrine reuptake inhibitor reboxetine: a review [J]. J Clin Psychiatry, 1998, 59(suppl 14): 4-7.

[2] Hajos M, Fleishaker JC, Filipiak-Reisner JK, et al. The selective norepinephrine reuptake inhibitor antidepressant reboxetine: pharmacological and clinical profile [J]. CNS Drug Rev, 2004, 10(1): 23-44.

[3] Jannuzzo MG, Pellizzoni C, Poggesi I, et al. Pharmacokinetics of reboxetine in healthy volunteers of different ages [J]. Eur Neuropsychopharm, 1995, 5(3): 300.

[4] Hughes B, McKenzie I, Stoker MJ. Use of (S,S)- or racemic reboxetine in medicament for treatment of pain conditions e.g. neuropathic pain, nociceptive pain and cancer pain: WO,

2006000903 [P]. 2006-05-01.

[5] lazzari E, Meroni M, Mazzini G, et al. Configurantional studies on 2[ γ-(2-ethoxyphenoxy)benzyl]morpholine fce-20124 [J]. Tetrahedron, 1985, 41(7): 1393-1399.

[6] Prabhakaran J, Majo VJ, Mann JJ, et al. Chiral synthesis of (2S,3S)-2-(2-morpholin-2-yl-2-phenylmethoxy)phenol [J]. Chirality, 2004, 16(3): 168-173.

[7] Raggi MA, Mandrioli R, Sabbioni C, et al. Separation of reboxetine enantiomers by means of capillary electrophoresis [J]. Electrophoresis, 2002, 23(12): 1870-1877.

[8] Ohman, D, Norlander, B, Peterson C, et al. Simultaneous determination of reboxetine and O-desethylreboxetine enantiomers using enantioselective reversed-phase highperformance liquid chromatography [J]. J Chromatogr A, 2002, 947(2): 247-254.

[9] Assaf G, Checksfield G, Critcher D, et al. The use of environmental metrics to evaluate green chemistry improvements to syntheses of (S,S)-reboxetine succinate [J]. Green

Chem, 2012, 14: 123-129.

[10] Henegar KE, Cebula M. Process development for (S,S)-reboxetine succinate via a Sharpless asymmetric epoxidation [J]. Org Process Res Dev, 2007, 11: 354-358.

[11] Harding WW, Hodge M, Wang Z. Enantioselective synthesis of (2R,3R) and (2S,3S)-2-[(3-chlorophenyl)-(2-methoxyphenoxy)methyl]morpholine [J]. Tetrahedron: Asymmetry, 2005, 16: 2249-2256.

[12] 邓 榴, 宓爱巧, 崔 欣, 等. 瑞波西汀关键中间体的合成[J]. 合成化学, 2001, 9(2): 93-95.

[13] Shu L, Shi Y. Asymmetric epoxidation using hydrogen peroxide(H2O2) as primary oxidant [J]. Tetrahedron Lett, 1999, 40(50): 8721-8724.

[14] Assaf G, Cansell G, Critcher D, et al. Application of a process friendly morpholine synthesis to (S,S)-reboxetine [J]. Tetrahedron Lett, 2010, 51: 5048-5051.

[15] Hayes ST, Assaf G, Checksfield G, et al. Commercial synthesis of (S,S)-reboxetine succinate: a journey to find the cheapest commercial chemistry for manufacture [J]. Org Process Res Dev, 2011, 15: 1305-1314.

[16] Reddy RS, Chouthaiwale PV, Suryavanshi G, et al. Co( Ⅲ ) ( salen) -catalyzed HKR of two stereocentered alkoxy- and azido epoxides: a concise enantioselective synthesis of (S,S)-reboxetine and (+)-epi-cytoxazone [J]. Chem Commun, 2010, 46: 5012-5014.

[17] Tokunaga M, larrow JF, Kakiuchi F, et al. Asymmetric catalysis with water: efficient kinetic resolution of terminal epoxides by means of catalytic hydrolysis [J]. Science, 1997,

277(5328): 936-938.

[18] Brenner E, Baldwin RM, Tamagnan G. Asymmetric synthesis of (+)-(S,S)-reboxetine via a new (S)-2-(hydroxymethyl) morpholine preparation [J]. Org Lett, 2005, 7: 937-939.

[19] Thomas-Xavier M, Domingo GP, Janine C. Syntheses of (S,S)-reboxetine via a catalytic stereospecific rearrangement of β-amino alcohols [J]. J Org Chem, 2008, 73(2): 707-710.

[20] Zeng F, Jarkas N, Stehouwer JS, et al. Synthesis, in vitro characterization, and radiolabeling of reboxetine analogs as potential PET radioligands for imaging the norepinephrine

transporter [J]. Bioorg Med Chem, 2008, 16(2): 783-793.

[21] Tamagnan GD, Alagille D. Norepinephrine transporter radiotracers and methods of syntheses thereof: WO, 2007 005935 [P]. 2007-01-11.

[22] Shafi A, SUmesh C. Enantioseletive synthesis of (+)-(S,S)-reboxetine [J]. Synlett, 2006, (11): 1771-1773.

[23] Fritz SP, Mumtaz A, Yar M, et al. Sulfinamides as highly effective amine protecting groups and their use in the conversion of amino alcohols into morpholines [J]. Eur J Org Chem, 2011, 17: 156-316.

[24] Akashi M, Arai N, Inoue T, et al. Catalyst-controlled diastereoselection in the hydrogenation of heterocycloalkyl ketones [J]. Adv Synth Catal, 2011, 353(11-12): 1955-1960.

112

Accesses

0

Citation

Detail

Sections
Recommended

/