Catalytic asymmetric total synthesis of the muscarinic receptor antagonist (R)-tolterodine

Advanced Synthesis and Catalysis

Volumn 347, Issue 5, 2005, Pages 662-666

  Hedberg, Christian ^a   Andersson, Pher G ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

Asymmetric synthesis; Me CBS catalyst; Sigmatropic rearrangement; Tolterodine; Total synthesis

Indexed keywords

6 METHYL 4 PHENYL 3,4 DIHYDROCHROMEN 2 ONE; CHROMENE DERIVATIVE; MUSCARINIC RECEPTOR BLOCKING AGENT; TOLTERODINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; CRYSTALLIZATION; ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; REDUCTION; SYNTHESIS;

EID: 18244393701     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404234     Document Type: Article

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14. 98% by weight by iodometric titration.
15. A similar approach to racemic tolterodine has been reported; see: N. A. Jonsson, B. A. Sparf, L. Mikiver, P. Moses, L. Nilvebrant, G. Glas, (Pharmacia & Upjohn Co.), European Patent EP 0325571, 1989.
16. This work has been reported in a patent, see: P. G. Andersson, C. Hedberg, (Pharmacia) WO 01049649, 2001.
17. Prepared according to the literature procedure, see: J. S. Swenton, K. Carpenter, Y. Chen, M. L. Kerns, W. Gary, J. Org. Chem. 1993, 58, 3308; analytical data consistent with those previously reported, see: D. M. McKinnon, A. Abouzeid, J. Heterocycl. Chem. 1991, 28, 347.
18. Prepared according to the literature procedure, see: J. S. Swenton, K. Carpenter, Y. Chen, M. L. Kerns, W. Gary, J. Org. Chem. 1993, 58, 3308; analytical data consistent with those previously reported, see: D. M. McKinnon, A. Abouzeid, J. Heterocycl. Chem. 1991, 28, 347.