Chemoenzymatic synthesis of (3S,4S)- and (3R,4R)-3-methoxy-4- methylaminopyrrolidine

Tetrahedron Letters

Volumn 45, Issue 43, 2004, Pages 8057-8059

  Kamal, Ahmed ^a   Shaik, Ahmad Ali ^a   Sandbhor, Mahendra ^a   Malik, M Shaheer ^a   Kaga, Harumi ^b  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 BENZYLOXYCARBONYL 3 PYRROLINE; 1 TERT BUTOXYCARBONYL 3 TERT BUTOXYCARBONYLAMINO 4 METHOXYPYRROLIDINE; 3 AZIDO 1 BENZYLOXYCARBONYL 4 HYDROXYPYRROLIDINE; 3 METHOXY 4 METHYLAMINOPYRROLIDINE; AG 7352; ANTINEOPLASTIC AGENT; BACTERIAL ENZYME; HYDROXYL GROUP; PYRROLIDINE DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; ENZYME MECHANISM; METHYLATION; REACTION ANALYSIS; RING CLOSING METATHESIS; TRANSESTERIFICATION;

EID: 4644316301     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.08.167     Document Type: Article

References (29)

1. A.B. Attyagalle, and D.E. Morgan Chem. Soc. Rev. 13 1984 245
2. G. Massiot, and C. Delaude A. Brossi The Alkaloids Vol. 27 1986 Academic New York Chapter 3
3. A. Numata, and T. Ibuka A. Brossi The Alkaloids Vol. 31 1987 Academic New York Chapter 6
4. A. Elbein, and R.I. Molyneux S.W. Pelletier The Alkaloids Vol. 5 1990 Academic New York Chapter 1
5. M. Pichon, and B. Figadere Tetrahedron: Asymmetry 7 1996 927
6. D. O'Hagan Nat. Prod. Rep. 14 1997 637
7. Y. Tsuzuki, K. Chiba, and K. Hino Tetrahedron: Asymmetry 12 2001 1739
8. Y. Tsuzuki, K. Chiba, and K. Hino Tetrahedron: Asymmetry 12 2001 2989
9. Tomita, K.; Tsuzuki, Y.; Shibamori, K.; Kashimoto, S.; Chiba, K. 217th ACS National Meeting, 1999; Abstract 249
10. Chiba, K.; Tsuzuki, Y.; Tomita, K.; Mizuno, K.; Sato, Y. 218th ACS National Meeting, 1999; Abstract 127
11. W.E. Kohlbrenner, N. Wideburg, D. Weigl, A. Saldivar, and D.T.W. Chu Antimicrob. Agents Chemother. 36 1992 81
12. M.J. Robinson, B.A. Martin, T.D. Gootz, P.R. Mcguirk, and N. Osheroff Antimicrob. Agents Chemother. 36 1992 751
13. M.P. Wentland, G.Y. Lesher, M. Reuman, M.D. Gruett, B. Singh, S.C. Aldous, P.H. Dorff, J.B. Rake, and S.A. Coughlin J. Med. Chem. 36 1993 2801
14. P.A. Permana, R.M. Snapka, L.L. Shen, D.T.W. Chu, J.J. Clement, and J.J. Plattner Biochemistry 33 1994 11333
15. T. Okada, K. Ezumi, M. Yamakawa, H. Sato, T. Tsuji, T. Tsushima, K. Motokawa, and Y. Komatsu Chem. Pharm. Bull. 41 1993 126
16. T. Okada, H. Sato, T. Tsuji, T. Tsushima, H. Nakai, T. Yoshida, and S. Matsuura Chem. Pharm. Bull. 41 1993 132
17. Y. Tsuzuki, K. Tomita, K. Shibamori, Y. Sato, S. Kashimoto, and K. Chiba J. Med. Chem. 47 2004 2097
18. A.R. Kumar, J.S. Reddy, and B.V. Rao Tetrahedron Lett. 44 2003 5687
19. A. Kamal, A.A. Shaik, M. Sandbhor, and M.S. Malik Tetrahedron: Asymmetry 15 2004 935 938
20. A. Kamal, and M. Sandbhor Biorg. Med. Chem. Lett. 12 2002 1735
21. A. Kamal, G.B.R. Khanna, R. Ramu, and T. Krishnaji Tetrahedron Lett. 44 2003 4783
22. A. Kamal, K.V. Ramana, and M.V. Rao J. Org. Chem. 66 2001 997
23. Different lipases were screened, among them Pseudomonas cepacia (PS-C) gives good enantioselectivity within 10 h compared to PS-D. Pseudomonas cepacia lipase (PS), Pseudomonas fluorescens (AK-20), Lipozyme immobilized from Mucor miehei, Candida rugosa lipase gave lower enantioselectivities. There were no significant conversions by employing lipases from Candida antartica, Porcine pancreas, and Candida cylindracea
24. A number of solvents such as diisopropyl ether, toluene, THF, tert-butyl methyl ether, and hexane were examined for this protocol. It was observed that diisopropyl ether was efficient for this lipase mediated resolution, whereas toluene takes longer (2 days) reaction times and gave comparatively low enantioselectivity. The results employing THF, tert-butyl methyl ether, and hexane were not satisfactory
25. General procedure for lipase mediated transesterification: To a solution of (±)-trans-3-azido-1-Cbz-4-hydroxypyrrolidine 7 (1 mmol) in diisopropyl ether (10 mL) was added lipase PS-C (1 equiv w/w), vinyl acetate (6 mmol). The suspension was shaken at 150 rpm at 40°C. The reaction mixture was monitored by chiral HPLC analysis until it reached about 50% conversion (10 h). The reaction was filtered and the filtrate was washed with water followed by brine. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography. The enantiopurity of the products (3S,4S)-7 and (3R,4R)-8 were determined by a chiral HPLC using Chiralcel OD column (hexane-isopropanol, 80:20) with 0.5 mL/min flow rate and compared with the corresponding racemic products
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