Enantioselective synthesis of D-threo-methylphenidate [8]

Journal of the American Chemical Society

Volumn 121, Issue 27, 1999, Pages 6511-6512

  Axten, Jeffrey M ^a   Ivy, Robert ^a   Krim, Lori ^a   Winkler, Jeffrey D ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

METHYLPHENIDATE;

CATALYSIS; CRYSTALLIZATION; DRUG SYNTHESIS; ENANTIOMER; LETTER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033553990     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991466o     Document Type: Letter

References (33)

1. Volkow, N.; Ding, Y.; Fowler, J.; Wang, O.; Logan, J.; Gatley, J.; Dewey, S.; Ashby, C.; Libermann, J.; Hitzemann, R.; Wolf, A. Arch. Gen. Psychiatry 1995, 52, 456.
2. Schweri, M.; Skolnick, P.; Rafferty, M.; Rice, K.; Janowsky, A.; Paul, S. J. Neurochem. 1985, 45, 1062.
3. (a) Prashad, M.; Har, D.; Ropic, O.; Blacklock, T. J.; Giannousis, P. Tetrahedron: Asymmetry 1998, 9, 2133.
4. (b) Faulconbridge, S.; Zavareh, H.; Evans, G.; Langston, M. PCT Int. Appl. Chem. Abstr. 1998, 129, 67705.
5. (c) Langsten, M.; Zavareh, H. PCT Int. Appl. Chem. Abstr. 1997, 127, 205477.
6. (d) Zavareh, H. PCT Int. Appl. Chem. Abstr. 1997, 127, 278144.
7. (a) Thai, D. L.; Sapko, M. T.; Reiter, C. T.; Bierer, D. E.; Perel, J. M. J. Med. Chem. 1998, 41, 591.
8. (b) Prashad, M.; Kim, H.; Lu, Y.; Har, D.; Repic, O.; Blacklock, T. J. Giannousis, P. J. Org. Chem. 1999, 64, 1750.
9. For excellent recent reviews of asymmetric reactions of diazo compounds, see: (a) Calter, M. Curr. Org. Chem. 1997, 1, 37. (b) Doyle, M.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; John Wiley & Sons: New York; 1998; Chapter 3.
10. For excellent recent reviews of asymmetric reactions of diazo compounds, see: (a) Calter, M. Curr. Org. Chem. 1997, 1, 37. (b) Doyle, M.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; John Wiley & Sons: New York; 1998; Chapter 3.
11. Presented in part at the 217th National Meeting of the American Chemical Society, Anaheim, CA, March 22, 1999; ORGN 142.
12. Doyle, M. P.; van Oeveren, A.; Westrum, L.; Protopopova, M.; Clayton, T. J. Am. Chem. Soc. 1991, 113, 8982.
13. Axten, J. M.; Krim, L.; Kung, H. F.; Winkler, J. D. J. Org. Chem. 1998, 63, 9628.
14. For examples of rhodium-mediated intramolecular C-H insertion reactions, see: (a) Watanabe, N.; Anada, M.; Hashimoto, S.; Ikegami, S. Synlett 1994, 1031. (b) Doyle, M. P.; Kalinin, A. Synlett 1995, 1075. (c) Sawamura, M.; Sasaki, H.; Nakata, T.; Ito, Y. Bull. Chem. Soc. Jpn. 1993, 66, 5. (d) Yakura, T.; Yamada, S.; Azuma, M.; Ueki, A.; Ikeda, M. Synthesis 1998, 973. (e) Hashimoto, S.; Watanabe, N.; Kawano, K.; Ikegami, S. Synth. Commun. 1994, 24, 3277. (f) Ye, T.; McKervey, M.; Brandes, B.; Doyle, M. P. Tetrahedron Lett. 1994, 35, 7269.
15. For examples of rhodium-mediated intramolecular C-H insertion reactions, see: (a) Watanabe, N.; Anada, M.; Hashimoto, S.; Ikegami, S. Synlett 1994, 1031. (b) Doyle, M. P.; Kalinin, A. Synlett 1995, 1075. (c) Sawamura, M.; Sasaki, H.; Nakata, T.; Ito, Y. Bull. Chem. Soc. Jpn. 1993, 66, 5. (d) Yakura, T.; Yamada, S.; Azuma, M.; Ueki, A.; Ikeda, M. Synthesis 1998, 973. (e) Hashimoto, S.; Watanabe, N.; Kawano, K.; Ikegami, S. Synth. Commun. 1994, 24, 3277. (f) Ye, T.; McKervey, M.; Brandes, B.; Doyle, M. P. Tetrahedron Lett. 1994, 35, 7269.
16. For examples of rhodium-mediated intramolecular C-H insertion reactions, see: (a) Watanabe, N.; Anada, M.; Hashimoto, S.; Ikegami, S. Synlett 1994, 1031. (b) Doyle, M. P.; Kalinin, A. Synlett 1995, 1075. (c) Sawamura, M.; Sasaki, H.; Nakata, T.; Ito, Y. Bull. Chem. Soc. Jpn. 1993, 66, 5. (d) Yakura, T.; Yamada, S.; Azuma, M.; Ueki, A.; Ikeda, M. Synthesis 1998, 973. (e) Hashimoto, S.; Watanabe, N.; Kawano, K.; Ikegami, S. Synth. Commun. 1994, 24, 3277. (f) Ye, T.; McKervey, M.; Brandes, B.; Doyle, M. P. Tetrahedron Lett. 1994, 35, 7269.
17. For examples of rhodium-mediated intramolecular C-H insertion reactions, see: (a) Watanabe, N.; Anada, M.; Hashimoto, S.; Ikegami, S. Synlett 1994, 1031. (b) Doyle, M. P.; Kalinin, A. Synlett 1995, 1075. (c) Sawamura, M.; Sasaki, H.; Nakata, T.; Ito, Y. Bull. Chem. Soc. Jpn. 1993, 66, 5. (d) Yakura, T.; Yamada, S.; Azuma, M.; Ueki, A.; Ikeda, M. Synthesis 1998, 973. (e) Hashimoto, S.; Watanabe, N.; Kawano, K.; Ikegami, S. Synth. Commun. 1994, 24, 3277. (f) Ye, T.; McKervey, M.; Brandes, B.; Doyle, M. P. Tetrahedron Lett. 1994, 35, 7269.
18. For examples of rhodium-mediated intramolecular C-H insertion reactions, see: (a) Watanabe, N.; Anada, M.; Hashimoto, S.; Ikegami, S. Synlett 1994, 1031. (b) Doyle, M. P.; Kalinin, A. Synlett 1995, 1075. (c) Sawamura, M.; Sasaki, H.; Nakata, T.; Ito, Y. Bull. Chem. Soc. Jpn. 1993, 66, 5. (d) Yakura, T.; Yamada, S.; Azuma, M.; Ueki, A.; Ikeda, M. Synthesis 1998, 973. (e) Hashimoto, S.; Watanabe, N.; Kawano, K.; Ikegami, S. Synth. Commun. 1994, 24, 3277. (f) Ye, T.; McKervey, M.; Brandes, B.; Doyle, M. P. Tetrahedron Lett. 1994, 35, 7269.
19. For examples of rhodium-mediated intramolecular C-H insertion reactions, see: (a) Watanabe, N.; Anada, M.; Hashimoto, S.; Ikegami, S. Synlett 1994, 1031. (b) Doyle, M. P.; Kalinin, A. Synlett 1995, 1075. (c) Sawamura, M.; Sasaki, H.; Nakata, T.; Ito, Y. Bull. Chem. Soc. Jpn. 1993, 66, 5. (d) Yakura, T.; Yamada, S.; Azuma, M.; Ueki, A.; Ikeda, M. Synthesis 1998, 973. (e) Hashimoto, S.; Watanabe, N.; Kawano, K.; Ikegami, S. Synth. Commun. 1994, 24, 3277. (f) Ye, T.; McKervey, M.; Brandes, B.; Doyle, M. P. Tetrahedron Lett. 1994, 35, 7269.
20. Doyle, M. P.; Winchester, W. R.; Hoorn, J.; Lynch, V.; Simonsen, S.; Ghosh, R. J. Am. Chem. Soc. 1993, 115, 9968.
21. For a recent example of rhodium mediated intermolecular C-H insertion, see: Davies, H.; Hansen, T. J. Am. Chem. Soc. 1997, 119, 9075.
22. Moritani, I.; Hosokawa, T.; Obata, N. J. Org. Chem. 1969, 34, 670.
23. Dieter, R. K.; Li, S. J. Org. Chem. 1997, 62, 7726.
24. Professor Huw Davies (State University of New York, Buffalo) has observed that the use of the rhodium prolinate catalyst described in ref 11 in this reaction leads to the formation of methylphenidate with attenuated diastereoselectivity. We thank him for sharing his results with us prior to publication.
25. Doyle, M. P.; Zhou, Q.-L.; Simonsen, S. H.; Lynch, V. Synlett 1996, 697.
26. Doyle, M. P.; Austin, R.; Bailey, A.; Dwyer, M.; Dyatlain, A.; Kalinan, A.; Kwai, M.; Liras, S.; Oalmann, C.; Pieters, R.; Protopopova, M.; Raab, C.; Roos, G.; Zhou, Q.; Martin S. J. Am. Chem. Soc. 1995, 117, 5763.
27. (a) Kennedy, M.; McKervey, M.; Maguire, A.; Roos, G. J. Chem. Soc., Chem. Commun. 1990, 361.
28. (b) McKervey, M.; Ye, T. J. Chem. Soc., Chem. Commun. 1992, 823.
29. (c) Doyle, M. P.; McKervey, M. A. J. Chem. Soc., Chem. Commun. 1997, 983.
30. Dakin, L.; Schaus, S.; Jacobsen, E.; Panek, J. Tetrahedron Lett. 1998, 39, 8947.
31. For calculations on these structures and a discussion of steric and electron effects in the C-H insertion reactions iazoacetates catalyzed by dirhodium, see: Doyle, M. P.; Westrum, L. J.; Wolthuis, W.; See, M.; Boone, W.; Bagheri, V.; Pearson, M. J. Am. Chem. Soc. 1993, 115, 958.
32. (a) Doyle, M. P.; Dyatkin, A.; Roos, G.; Canas, F.; Pierson, D.; van Basten, A.; Muller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507.
33. (b) Muller, P.; Polleux, P. Helv. Chim. Acta 1994, 77, 645.