Chemo-enzymatic preparation of chiral 3-aminopyrrolidine derivatives

Tetrahedron

Volumn 60, Issue 3, 2004, Pages 647-653

  Iding, Hans ^a   Wirz, Beat ^a   Rogers Evans, Mark ^a  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

Biotransformation; D asparagine; Enantioselective; Enzyme; Hydrolysis; L asparagine; Protease; Resolution

Indexed keywords

ASPARAGINE; ESTER DERIVATIVE; PROTEINASE; PYRROLIDINE DERIVATIVE; SOLVENT;

ARTICLE; CYCLIZATION; DEPROTECTION REACTION; ENANTIOSELECTIVITY; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME SUBSTRATE; HYDROLYSIS; PH; PRIORITY JOURNAL; PRODUCTIVITY; RACEMIZATION; REDUCTION;

EID: 0346334551     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.10.118     Document Type: Article

References (29)

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11. For our initial disclosures for the preparation of (R)-1-benzyl- pyrrolidin-3-ylamine, see: (a) Rogers-Evans, M. WO 0214332, 2002. Iding, H.; Rogers-Evans, M.; Wirz, B. EP 1148140 A1, 2001. (c) For previous routes to (R)-1-benzyl-pyrrolidin-3-ylamine, see via N-formyl-D-aspartic acid anhydride (c): Ohno, K.; Sato, H. JP 2002371057, 2002. (d) Via diastereoselective Schiff base formation: Sakai, T. JP 2001226349, 2001. (e) . Via azide displacement of mesylate: Einsiedel J., Thomas C., Hubner H., Gmeiner P. Bioorg. Med. Chem. Lett. 10:2000;2041-2044 (f) Via resolution of racemate: Sakai, T.; Hashimoto, K. JP 09176115, 1997. (g) Via Mitsunobu on alcohol: Sanchez, J. EP 304087, 1989.
12. For our initial disclosures for the preparation of (R)-1-benzyl- pyrrolidin-3-ylamine, see: (a) Rogers-Evans, M. WO 0214332, 2002. Iding, H.; Rogers-Evans, M.; Wirz, B. EP 1148140 A1, 2001. (c) For previous routes to (R)-1-benzyl-pyrrolidin-3-ylamine, see via N-formyl-D-aspartic acid anhydride (c): Ohno, K.; Sato, H. JP 2002371057, 2002. (d) Via diastereoselective Schiff base formation: Sakai, T. JP 2001226349, 2001. (e) . Via azide displacement of mesylate: Einsiedel J., Thomas C., Hubner H., Gmeiner P. Bioorg. Med. Chem. Lett. 10:2000;2041-2044 (f) Via resolution of racemate: Sakai, T.; Hashimoto, K. JP 09176115, 1997. (g) Via Mitsunobu on alcohol: Sanchez, J. EP 304087, 1989.
13. For our initial disclosures for the preparation of (R)-1-benzyl- pyrrolidin-3-ylamine, see: (a) Rogers-Evans, M. WO 0214332, 2002. Iding, H.; Rogers-Evans, M.; Wirz, B. EP 1148140 A1, 2001. (c) For previous routes to (R)-1-benzyl-pyrrolidin-3-ylamine, see via N-formyl-D-aspartic acid anhydride (c): Ohno, K.; Sato, H. JP 2002371057, 2002. (d) Via diastereoselective Schiff base formation: Sakai, T. JP 2001226349, 2001. (e) . Via azide displacement of mesylate: Einsiedel J., Thomas C., Hubner H., Gmeiner P. Bioorg. Med. Chem. Lett. 10:2000;2041-2044 (f) Via resolution of racemate: Sakai, T.; Hashimoto, K. JP 09176115, 1997. (g) Via Mitsunobu on alcohol: Sanchez, J. EP 304087, 1989.
14. For our initial disclosures for the preparation of (R)-1-benzyl- pyrrolidin-3-ylamine, see: (a) Rogers-Evans, M. WO 0214332, 2002. Iding, H.; Rogers-Evans, M.; Wirz, B. EP 1148140 A1, 2001. (c) For previous routes to (R)-1-benzyl-pyrrolidin-3-ylamine, see via N-formyl-D-aspartic acid anhydride (c): Ohno, K.; Sato, H. JP 2002371057, 2002. (d) Via diastereoselective Schiff base formation: Sakai, T. JP 2001226349, 2001. (e) . Via azide displacement of mesylate: Einsiedel J., Thomas C., Hubner H., Gmeiner P. Bioorg. Med. Chem. Lett. 10:2000;2041-2044 (f) Via resolution of racemate: Sakai, T.; Hashimoto, K. JP 09176115, 1997. (g) Via Mitsunobu on alcohol: Sanchez, J. EP 304087, 1989.
15. For our initial disclosures for the preparation of (R)-1-benzyl- pyrrolidin-3-ylamine, see: (a) Rogers-Evans, M. WO 0214332, 2002. Iding, H.; Rogers-Evans, M.; Wirz, B. EP 1148140 A1, 2001. (c) For previous routes to (R)-1-benzyl-pyrrolidin-3-ylamine, see via N-formyl-D-aspartic acid anhydride (c): Ohno, K.; Sato, H. JP 2002371057, 2002. (d) Via diastereoselective Schiff base formation: Sakai, T. JP 2001226349, 2001. (e) . Via azide displacement of mesylate: Einsiedel J., Thomas C., Hubner H., Gmeiner P. Bioorg. Med. Chem. Lett. 10:2000;2041-2044 (f) Via resolution of racemate: Sakai, T.; Hashimoto, K. JP 09176115, 1997. (g) Via Mitsunobu on alcohol: Sanchez, J. EP 304087, 1989.
16. For our initial disclosures for the preparation of (R)-1-benzyl- pyrrolidin-3-ylamine, see: (a) Rogers-Evans, M. WO 0214332, 2002. Iding, H.; Rogers-Evans, M.; Wirz, B. EP 1148140 A1, 2001. (c) For previous routes to (R)-1-benzyl-pyrrolidin-3-ylamine, see via N-formyl-D-aspartic acid anhydride (c): Ohno, K.; Sato, H. JP 2002371057, 2002. (d) Via diastereoselective Schiff base formation: Sakai, T. JP 2001226349, 2001. (e) . Via azide displacement of mesylate: Einsiedel J., Thomas C., Hubner H., Gmeiner P. Bioorg. Med. Chem. Lett. 10:2000;2041-2044 (f) Via resolution of racemate: Sakai, T.; Hashimoto, K. JP 09176115, 1997. (g) Via Mitsunobu on alcohol: Sanchez, J. EP 304087, 1989.
17. For our initial disclosures for the preparation of (R)-1-benzyl- pyrrolidin-3-ylamine, see: (a) Rogers-Evans, M. WO 0214332, 2002. Iding, H.; Rogers-Evans, M.; Wirz, B. EP 1148140 A1, 2001. (c) For previous routes to (R)-1-benzyl-pyrrolidin-3-ylamine, see via N-formyl-D-aspartic acid anhydride (c): Ohno, K.; Sato, H. JP 2002371057, 2002. (d) Via diastereoselective Schiff base formation: Sakai, T. JP 2001226349, 2001. (e) . Via azide displacement of mesylate: Einsiedel J., Thomas C., Hubner H., Gmeiner P. Bioorg. Med. Chem. Lett. 10:2000;2041-2044 (f) Via resolution of racemate: Sakai, T.; Hashimoto, K. JP 09176115, 1997. (g) Via Mitsunobu on alcohol: Sanchez, J. EP 304087, 1989.
18. For a recent selection, see: (a) Mattson, M.; Vojkovsky, T.; Liang, C.; Tang, P.-C.; Guan, H. WO 0331438, 2003. Ghosh, S.; Patane, M.; Carson, K. G.; Chi, S.; Ye, Q.; Elder, A.; Jenkins, T. WO 0337271, 2003. (c) Ito, F.; Koike, H.; Sudo, M.; Yamagishi, T.; Ando, K. WO 0300677, 2003. (d) Chu, S.; Alegria, L.; Bleckman, T.; Chong, W.; Duvadie, R.; Li, L.; Reich, S.; Romines, W.; Wallace, M.; Yang, Y. WO 0304467, 2003. (e) Keegan, K.; Kesicki, E.; Gaudino, J.; Cook, A.; Cowen, S.; Burgess, L. WO 0270494, 2002. (f) Burns, C.; Wilks, A. WO 0260492, 2002. (g) Mantell, S.; Monaghan, S.; Stephenson, P. WO 0200676, 2002. (h) Igarashi, N. JP 2003073352, 2002. (i) Caulfield W., Collie I., Dickins R., Epemolu O., McGuire R., Hill D., McVey G., Morphy R., Rankovic Z., Sundaram H. J. Med. Chem. 44:2001;2679-2682.
19. For a recent selection, see: (a) Mattson, M.; Vojkovsky, T.; Liang, C.; Tang, P.-C.; Guan, H. WO 0331438, 2003. Ghosh, S.; Patane, M.; Carson, K. G.; Chi, S.; Ye, Q.; Elder, A.; Jenkins, T. WO 0337271, 2003. (c) Ito, F.; Koike, H.; Sudo, M.; Yamagishi, T.; Ando, K. WO 0300677, 2003. (d) Chu, S.; Alegria, L.; Bleckman, T.; Chong, W.; Duvadie, R.; Li, L.; Reich, S.; Romines, W.; Wallace, M.; Yang, Y. WO 0304467, 2003. (e) Keegan, K.; Kesicki, E.; Gaudino, J.; Cook, A.; Cowen, S.; Burgess, L. WO 0270494, 2002. (f) Burns, C.; Wilks, A. WO 0260492, 2002. (g) Mantell, S.; Monaghan, S.; Stephenson, P. WO 0200676, 2002. (h) Igarashi, N. JP 2003073352, 2002. (i) Caulfield W., Collie I., Dickins R., Epemolu O., McGuire R., Hill D., McVey G., Morphy R., Rankovic Z., Sundaram H. J. Med. Chem. 44:2001;2679-2682.
20. For a recent selection, see: (a) Mattson, M.; Vojkovsky, T.; Liang, C.; Tang, P.-C.; Guan, H. WO 0331438, 2003. Ghosh, S.; Patane, M.; Carson, K. G.; Chi, S.; Ye, Q.; Elder, A.; Jenkins, T. WO 0337271, 2003. (c) Ito, F.; Koike, H.; Sudo, M.; Yamagishi, T.; Ando, K. WO 0300677, 2003. (d) Chu, S.; Alegria, L.; Bleckman, T.; Chong, W.; Duvadie, R.; Li, L.; Reich, S.; Romines, W.; Wallace, M.; Yang, Y. WO 0304467, 2003. (e) Keegan, K.; Kesicki, E.; Gaudino, J.; Cook, A.; Cowen, S.; Burgess, L. WO 0270494, 2002. (f) Burns, C.; Wilks, A. WO 0260492, 2002. (g) Mantell, S.; Monaghan, S.; Stephenson, P. WO 0200676, 2002. (h) Igarashi, N. JP 2003073352, 2002. (i) Caulfield W., Collie I., Dickins R., Epemolu O., McGuire R., Hill D., McVey G., Morphy R., Rankovic Z., Sundaram H. J. Med. Chem. 44:2001;2679-2682.
21. For a recent selection, see: (a) Mattson, M.; Vojkovsky, T.; Liang, C.; Tang, P.-C.; Guan, H. WO 0331438, 2003. Ghosh, S.; Patane, M.; Carson, K. G.; Chi, S.; Ye, Q.; Elder, A.; Jenkins, T. WO 0337271, 2003. (c) Ito, F.; Koike, H.; Sudo, M.; Yamagishi, T.; Ando, K. WO 0300677, 2003. (d) Chu, S.; Alegria, L.; Bleckman, T.; Chong, W.; Duvadie, R.; Li, L.; Reich, S.; Romines, W.; Wallace, M.; Yang, Y. WO 0304467, 2003. (e) Keegan, K.; Kesicki, E.; Gaudino, J.; Cook, A.; Cowen, S.; Burgess, L. WO 0270494, 2002. (f) Burns, C.; Wilks, A. WO 0260492, 2002. (g) Mantell, S.; Monaghan, S.; Stephenson, P. WO 0200676, 2002. (h) Igarashi, N. JP 2003073352, 2002. (i) Caulfield W., Collie I., Dickins R., Epemolu O., McGuire R., Hill D., McVey G., Morphy R., Rankovic Z., Sundaram H. J. Med. Chem. 44:2001;2679-2682.
22. For a recent selection, see: (a) Mattson, M.; Vojkovsky, T.; Liang, C.; Tang, P.-C.; Guan, H. WO 0331438, 2003. Ghosh, S.; Patane, M.; Carson, K. G.; Chi, S.; Ye, Q.; Elder, A.; Jenkins, T. WO 0337271, 2003. (c) Ito, F.; Koike, H.; Sudo, M.; Yamagishi, T.; Ando, K. WO 0300677, 2003. (d) Chu, S.; Alegria, L.; Bleckman, T.; Chong, W.; Duvadie, R.; Li, L.; Reich, S.; Romines, W.; Wallace, M.; Yang, Y. WO 0304467, 2003. (e) Keegan, K.; Kesicki, E.; Gaudino, J.; Cook, A.; Cowen, S.; Burgess, L. WO 0270494, 2002. (f) Burns, C.; Wilks, A. WO 0260492, 2002. (g) Mantell, S.; Monaghan, S.; Stephenson, P. WO 0200676, 2002. (h) Igarashi, N. JP 2003073352, 2002. (i) Caulfield W., Collie I., Dickins R., Epemolu O., McGuire R., Hill D., McVey G., Morphy R., Rankovic Z., Sundaram H. J. Med. Chem. 44:2001;2679-2682.
23. For a recent selection, see: (a) Mattson, M.; Vojkovsky, T.; Liang, C.; Tang, P.-C.; Guan, H. WO 0331438, 2003. Ghosh, S.; Patane, M.; Carson, K. G.; Chi, S.; Ye, Q.; Elder, A.; Jenkins, T. WO 0337271, 2003. (c) Ito, F.; Koike, H.; Sudo, M.; Yamagishi, T.; Ando, K. WO 0300677, 2003. (d) Chu, S.; Alegria, L.; Bleckman, T.; Chong, W.; Duvadie, R.; Li, L.; Reich, S.; Romines, W.; Wallace, M.; Yang, Y. WO 0304467, 2003. (e) Keegan, K.; Kesicki, E.; Gaudino, J.; Cook, A.; Cowen, S.; Burgess, L. WO 0270494, 2002. (f) Burns, C.; Wilks, A. WO 0260492, 2002. (g) Mantell, S.; Monaghan, S.; Stephenson, P. WO 0200676, 2002. (h) Igarashi, N. JP 2003073352, 2002. (i) Caulfield W., Collie I., Dickins R., Epemolu O., McGuire R., Hill D., McVey G., Morphy R., Rankovic Z., Sundaram H. J. Med. Chem. 44:2001;2679-2682.
24. For a recent selection, see: (a) Mattson, M.; Vojkovsky, T.; Liang, C.; Tang, P.-C.; Guan, H. WO 0331438, 2003. Ghosh, S.; Patane, M.; Carson, K. G.; Chi, S.; Ye, Q.; Elder, A.; Jenkins, T. WO 0337271, 2003. (c) Ito, F.; Koike, H.; Sudo, M.; Yamagishi, T.; Ando, K. WO 0300677, 2003. (d) Chu, S.; Alegria, L.; Bleckman, T.; Chong, W.; Duvadie, R.; Li, L.; Reich, S.; Romines, W.; Wallace, M.; Yang, Y. WO 0304467, 2003. (e) Keegan, K.; Kesicki, E.; Gaudino, J.; Cook, A.; Cowen, S.; Burgess, L. WO 0270494, 2002. (f) Burns, C.; Wilks, A. WO 0260492, 2002. (g) Mantell, S.; Monaghan, S.; Stephenson, P. WO 0200676, 2002. (h) Igarashi, N. JP 2003073352, 2002. (i) Caulfield W., Collie I., Dickins R., Epemolu O., McGuire R., Hill D., McVey G., Morphy R., Rankovic Z., Sundaram H. J. Med. Chem. 44:2001;2679-2682.
25. For a recent selection, see: (a) Mattson, M.; Vojkovsky, T.; Liang, C.; Tang, P.-C.; Guan, H. WO 0331438, 2003. Ghosh, S.; Patane, M.; Carson, K. G.; Chi, S.; Ye, Q.; Elder, A.; Jenkins, T. WO 0337271, 2003. (c) Ito, F.; Koike, H.; Sudo, M.; Yamagishi, T.; Ando, K. WO 0300677, 2003. (d) Chu, S.; Alegria, L.; Bleckman, T.; Chong, W.; Duvadie, R.; Li, L.; Reich, S.; Romines, W.; Wallace, M.; Yang, Y. WO 0304467, 2003. (e) Keegan, K.; Kesicki, E.; Gaudino, J.; Cook, A.; Cowen, S.; Burgess, L. WO 0270494, 2002. (f) Burns, C.; Wilks, A. WO 0260492, 2002. (g) Mantell, S.; Monaghan, S.; Stephenson, P. WO 0200676, 2002. (h) Igarashi, N. JP 2003073352, 2002. (i) Caulfield W., Collie I., Dickins R., Epemolu O., McGuire R., Hill D., McVey G., Morphy R., Rankovic Z., Sundaram H. J. Med. Chem. 44:2001;2679-2682.
26. For a recent selection, see: (a) Mattson, M.; Vojkovsky, T.; Liang, C.; Tang, P.-C.; Guan, H. WO 0331438, 2003. Ghosh, S.; Patane, M.; Carson, K. G.; Chi, S.; Ye, Q.; Elder, A.; Jenkins, T. WO 0337271, 2003. (c) Ito, F.; Koike, H.; Sudo, M.; Yamagishi, T.; Ando, K. WO 0300677, 2003. (d) Chu, S.; Alegria, L.; Bleckman, T.; Chong, W.; Duvadie, R.; Li, L.; Reich, S.; Romines, W.; Wallace, M.; Yang, Y. WO 0304467, 2003. (e) Keegan, K.; Kesicki, E.; Gaudino, J.; Cook, A.; Cowen, S.; Burgess, L. WO 0270494, 2002. (f) Burns, C.; Wilks, A. WO 0260492, 2002. (g) Mantell, S.; Monaghan, S.; Stephenson, P. WO 0200676, 2002. (h) Igarashi, N. JP 2003073352, 2002. (i) Caulfield W., Collie I., Dickins R., Epemolu O., McGuire R., Hill D., McVey G., Morphy R., Rankovic Z., Sundaram H. J. Med. Chem. 44:2001;2679-2682.
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