Chlorination/cyclodehydration of amino alcohols with SOCl2: An old reaction revisited

Journal of Organic Chemistry

Volumn 73, Issue 1, 2008, Pages 312-315

  Xu, Feng ^a   Simmons, Bryon ^a   Reamer, Robert A ^a   Corley, Edward ^a   Murry, Jerry ^a   Tschaen, David ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ALCOHOLS; CLASSICAL N-PROTECTION; CYCLODEHYDRATION; DEPROTECTION SEQUENCE;

AMINES; AMINO ACIDS; CHLORINATION; CYCLIZATION; DEHYDRATION; REACTION KINETICS;

ALCOHOLS;

AMINOALCOHOL; SULFUR DERIVATIVE; THIONYL CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHLORINATION; CYCLIZATION; CYCLODEHYDRATION; DEPROTECTION REACTION; ONE POT SYNTHESIS; REACTION ANALYSIS;

AMINO ALCOHOLS; CYCLIZATION; DEHYDRATION; HALOGENATION; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFUR OXIDES;

EID: 37549042327     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701877h     Document Type: Article

References (64)

1. For recent reviews, see: (a) Buffat, M. G. P. Tetrahedron 2004, 60, 1701.
2. (b) Larock, R. C. Comprehensive Organic Transformations, 2nd ed.; Wiley-VCH: New York, 1999; pp 689-702 and 779-784.
3. For recent examples and applications, see: (a) Smith, A. B., III; Kim, D.-S. J. Org. Chem. 2006, 71, 2547.
4. (b) Trost, B. M.; Tang, W.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 14785.
5. (c) Pyne, S. G.; Davis, A. S.; Gates, N. J.; Hartley, J. P.; Lindsay, K. B.; Machan, T.; Tang, M. Synlett 2004, 2670.
6. (d) Kan, T.; Kobayshi, H.; Fukuyama, T. Synlett 2002, 697.
7. (e) Ina, H.; Kibayashi, C. J. Org. Chem. 1993, 58, 52.
8. (f) Burgess, K.; Chaplin, D. A.; Henderson, I.; Pan, Y. T.; Elbein, A. D. J. Org. Chem. 1992, 57, 1103.
9. (g) Schink, H. E.; Pettersson, H.; Bäckvall, J.-E. J. Org. Chem. 1991, 56, 2769.
10. For recent applications of direct cyclodehydration methods, see: (a) de Figueiredo, R. M.; Fröhlich, R.; Christmann, M. J. Org. Chem. 2006, 71, 4147.
11. (b) Wu, T. R.; Chong, J. M. J. Am. Chem. Soc. 2006, 128, 9646.
12. (c) Pulz, R.; Al-Harrasi, A.; Reissig, H.-U. Org. Lett. 2002, 4, 2353 and references cited therein.
13. (a) Nota, T.; Murahashi, S.-I. Synlett 1991, 693.
14. (b) Murahashi, S.-I.; Kondo, K.; Hakata, T. Tetrahedron Lett. 1982, 23, 229.
15. (c) Grigg, R.; Mitchell, T. R. B.; Sutthivaiyakit S.; Tongpenyai, N. Chem. Commun. 1981, 611.
16. For examples, see: (a) Tanaka, H.; Murakami, Y.; Aizawa, T.; Torii, S. Bull. Chem. Soc. Jpn. 1989, 62, 3742.
17. (b) Papageorgiou, C.; Borer, X. Helv. Chim. Acta 1988, 71, 1079.
18. For recent reviews, see: (a) Hughes, D. L. Org. Prep. Proc. Int. 1996, 28, 127.
19. (b) Hughes, D. L. Org. React. 1992, 42, 335.
20. (c) Mitsunobu, O. Synthesis 1981, 1.
21. For reviews, see: (a) Castro, B. R. Org. React. 1983, 29, 1.
22. (b) Appel, R. Angew. Chem., Int. Ed. Engl. 1975, 14, 801.
23. 2, see: (a) El-Sakka, I. A.; Hassan, N. A. J. Sulfur Chem. 2005, 26, 33.
24. (b) Wirth, D. D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1995; p 4873.
25. (c) Oka, K. Synthesis 1981, 661.
26. 8
27. For example, see: Pilkington, M.; Wallis, J. D. Chem. Commun. 1993, 1857.
28. For examples of chlorination of amino alcohol salts, see: (a) Back, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543.
29. (b) Bubnov, Y. N.; Zykov, A. Y.; Ignatenko, A. V.; Mikhailovsky, A. G.; Shklyaev, Y. V.; Shklyaev, V. S. Izv. Akad. Nauk., Ser. Khim. 1996, 935.
30. (c) Dobler, M.; Beerli, R.; Weissmahr, W. K.; Borschberg, H.-J. Tetrahedron: Asymmetry 1992, 11, 1411.
31. (d) Kobor, J.; Fülöp, F.; Bernáth, G.; Sohár, P. Tetrahedron 1987, 43, 1887.
32. (e) Bäckvall, J. E.; Renko, Z. D.; Byström, S. E. Tetrahedron Lett. 1987, 28, 4199.
33. (f) Piper, J. R.; Johnston, T. P. J. Org. Chem. 1963, 28, 981.
34. (g) Norton, T. R.; Seibert, R. A.; Benson, A. A.; Bergstrom, F. W. J. Am. Chem. Soc. 1946, 68, 1572.
35. Xu, F.; Murry, J. A.; Simmons, B.; Corley, E.; Fitch, K.; Karady, S.; Tschaen, D. Org. Lett. 2006, 8, 3885.
36. Gerrard, W. J. Chem. Soc. 1940, 218
37. For examples, see: (a) Lu, B. Z.; Jin, F.; Zhang, Y.; Wu, X.; Wald, S. A.; Senanayake, C. H. Org. Lett. 2005, 7, 1465.
38. (b) Benson, S. C.; Snyder, J. K. Tetrahedron Lett. 1991, 32, 5885.
39. (c) Lowe, G.; Reed, M. A. Tetrahedron: Asymmetry 1990, 1, 885.
40. 2 in the presence of bases, see: (a) Muratake, H.; Natsume, M. Tetrahedron Lett 2002, 43, 2913.
41. (b) Howarth, N. M.; Malpass, J. R.; Smith, C. R. Tetrahedron 1998, 54, 10899.
42. (c) Bosch, J.; Mestre, E.; Bonjoch, J.; López, F.; Granados, R. Heterocycles 1984, 22, 767.
43. (d) Mousseron, M.; Winternitz, F.; Mousseron-Canet, M. Bull. Soc. Chim. Fr. 1953, 737.
44. 2 to amino alcohol solution, see: (a) Gursky, M. E.; Ponomarev, V. A.; Pershin, D. G.; Bubnov, Y. N.; Antipin, M. Y.; Lyssenko, K. A. Russ. Chem. Bull. 2002, 51, 1562.
45. (b) Foubelo, F.; Gómez, C.; Gutiérrez, A.; Yus, M. J. Heterocycl. Chem. 2000, 37, 1061.
46. (c) Howarth, N. M.; Malpass, J. R.; Smith, C. R. Tetrahedron 1998, 54, 10899.
47. (d) Gursky, M. E.; Potapova, T. V.; Bubnov, Y. N. Izv. Akad. Nauk., Ser Khim. 1998, 1450.
48. (e) Bubnov, Y. N.; Zykov, A. Y.; Ignatenko, A. V.; Mikhailovsky, A. G.; Shklyaev, Y. V.; Shklyaev, V. S. Izv. Akad. Nauk., Ser Khim. 1996, 935.
49. (f) Granier, C.; Guilard, R. Tetrahedron 1995, 51, 1197.
50. (g) Grigg, R.; Santhakumar, V.; Sridharan, V.; Thornton-Pett, M.; Brideg, A. W. Tetreahedron 1993, 49, 5177.
51. (h) Takano, S.; Inomata, K.; Sato, T.; Ogasawara, K. Chem. Commun. 1989, 1591.
52. (i) Barbry, D.; Couturier, D.; Ricart, G. Synthesis 1980, 387.
53. (j) Sturm, P. A.; Cory, M.; Henry, D. W. J. Med. Chem. 1977, 20, 1333.
54. (k) Giacet, C.; Bécue, G. C. R. Acad. Sci., C 1967, 264, 103.
55. 8,14
56. Although a slurry was obtained after prolonged agitation of the reaction mixture at ambient temperature, the precipitation of the HCl salt, which can be isolated and characterized, was believed to be a result of sojubility-driven equilibrium shift. See more discussion in the text.
57. 3.
58. The formation of possible sulfamide intermediate I was not observed. (Chemical Equation Presented)
59. 2.
60. is commercially available. For leading references of the synthesis of crispine A, see: (a) King, F. D. Tetrahedron 2007, 63, 2053.
61. (b) Knöelker, H.-J.; Agarwal, S. Tetrahedron Lett. 2005, 46, 1173.
62. For examples of relative rates of cyclization as a function of ring size, see: (a) Mandolini, L. Adv. Phys. Org. Chem. 1986, 22, 1.
63. (b) Winnik M. A. Chem. Rev. 1981, 81, 491.
64. (c) Galli, C.; Illuminati, G.; Mandolini, L.; Tamborra, P. J. Am. Chem. Soc. 1977, 99, 2591.