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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 11
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Original Articles

Rearrangement of Ethers: A New Route to Tolterodine

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Pages 1565-1571 | Received 08 Jan 2010, Published online: 20 Apr 2011

REFERENCES

  • (a) Yoo , K. ; Kim , H. ; Yun , J. Enantioselective synthesis of (R)-tolterodine via CuH-catalyzed asymmetric conjugate reduction . J. Org. Chem. 2009 , 74 , 4232 ; (b) Kobayashi , K. ; Nishikata , T. ; Yamamoto , Y. ; Miyaura , N. Stepwise palladium-catalyzed 1,4-addition of arylboronic acids to enones and regioselective Baeyer–Villiger oxidation for enantioselective synthesis of β-diaryl esters and (+)-(R)-tolterodine . Bull. Chem. Soc. Jpn. 2008 , 1019 ; (c) Sorgel , S.; Tokunaga. N. ; Sasaki , K. ; Okamoto , K. ; Hayashi , T. Rhodium/chiral diene-catalyzed asymmetric 1,4-addition of arylboronic acids to arylmethylene cyanoacetates . Org. Lett. 2008 , 10 , 589 ; (d) Ulgheri , F. ; Marchetti , M. ; Piccolo , O. Enantioselective synthesis of (S)- and (R)-tolterodine by asymmetric hydrogenation of a coumarin derivative obtained by a Heck reaction . J. Org. Chem. 2007 , 72 , 6056 ; (e) Hedberg , C. ; Andersson , P. G. Catalytic asymmetric total synthesis of the muscarinic receptor antagonist (R)-tolterodine . Adv. Synth. Catal. 2005 , 347 , 662 ; (f) Chen , G. ; Tokunaga , N. ; Hayashi , T. Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins: Asymmetric synthesis of (R)-tolterodine . Org. Lett. 2005 , 7 , 2285 ; (g) Brian , D. G. ; Benjamin , R. T. ; Bruce , H. L. Asymmetric conjugate reductions of coumarins: A new route to tolterodine and related coumarin derivatives . Org. Lett. 2009 , 11 , 5374 .
  • (a) Johnsson , N. A. ; Sparf , B. A. ; Mikiver , L. ; Moses , P. ; Nilvebrant , L. ; Glas , G. (Pharmacia and Upjohn Co.) New amines, their use and preparation. EP 0325571, 1989; U.S. Patent 5,382,600 ; (b) Gage , J. R. ; Cabaj , J. E. (Pharmacia and Upjohn Co.). Process to Prepare Tolterodine. U.S. Patent 5,922,914, 1999 ; (c) Mathad , V. T. ; Venkataraman , S. ; Kumari , R. L. ; Arunagiri , M. ; Reddy , C. R. ; Ramakrishna , M. ; Reddy , K. S. ; Srinivasan , N. ; Srinivas , K. An improved, scalable, and impurity-free process for tolterodine tartrate . Org. Process. Res. Dev. 2005 , 9 , 314 ; (d) Rhee , H. ; Park , S. ; Park , D. ; Ko , J. ; De Castro , K. A. Reduction of ethyl benzoylacetate and selective protection of 2-(3-hydroxy-1-phenylpropyl)-4-methylphenol: A new and facile synthesis of tolterodine . Org. Process. Res. Dev. 2007 , 11 , 918 ; (e) De Castro , K. A. ; Rhee , H. Selective nosylation of 1-phenylpropane-1,3-diol and perchloric acid mediated Friedel–Crafts alkylation: Key steps for the new and straightforward synthesis of tolterodine . Synthesis 2008 , 1841 ; (f) Gabriele , R. ; Sesto , S. ; Simone , M. ; Roberto , R. ; Pietro , A. Process for the preparation of tolterodine. U.S. Patent 0097127, 2008 ; (g) Yatendra , K. ; Mohan , P. ; Praveen , K. N. ; Satyananda , M. Process for the preparation of tolterodine. U.S. Patent 6,822,119, 2004 .
  • Veera Reddy , A. ; Udaya , B. R. S. ; Sreenivasula , R. B. Novel acid-catalyzed rearrangement of duloxetine. Indian J. Chem. 2007, 46B, 1695.

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