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A short synthesis of 4-amino-3-hydroxybutyric acid (GABOB) via allyl cyanide

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Abstract

4-Amino-3-hydroxybutyric acid was synthesized from allyl cyanide in four steps in an overall yield of 38%. Ultrasonically promoted epoxidation of allyl cyanide with m-chloroperoxybenzoic acid giving oxiranylacetonitrile was used as a key step.

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References

  1. D. S. Bose and M. K. Gurjar, Synth. Commun., 1989, 19, 3313; (b) Y. N. Bubnov, L. I. Lavrinovich, A. Y. Zykov, and A. V. Ignatenko, Mendeleev Commun., 1992, 86.

    Google Scholar 

  2. E. García-Flores and R. Farías, Stereotact. Funct. Neurosurg., 1997, 69, 243; (b) R. Chemello, D. Giaretta, A. Pellegrini, and G. Testa, Riv. Neurol., 1980, 50, 253; (c) A. Tartara, A. Arrigo, C. Scamoni, and A. Presazzi, Minerva Med., 1973, 64, 1943; (d) S. Banfi, W. Fonio, E. Allievi, and S. Raimondo, Pharmacol. Res. Commun., 1983, 15, 553.

    Google Scholar 

  3. M. A. Enero, D. Solignac, and J. A. Apud, Clin. Exp. Hypertens A, 1988, 10, Suppl 1, 331; (b) K. Kamei, Toho Igakkai Zasshi, 1978, 25, 64; Chem. Abstr., 1978, 89, 140626.

    Google Scholar 

  4. J. Nakao, T. Hasegawa, H. Hashimoto, T. Noto, and T. Nakajima, Pharmacol. Biochem. Behav., 1991, 40, 359; (b) J. Nakao, Kyoto-furitsu Ika Daigaku Zasshi, 1990, 99, 57; Chem. Abstr., 1990, 113, 71657; (c) K. Matsushita, L. R. Gjessing, T. Shinka, and I. Matsumoto, Iyo Masu Kenkyukai Koenshu, 1979, 4, 269; Chem. Abstr., 1980, 92, 142809; (d) G. Nistico, Int. J. Clin. Pharmacol. Biopharm., 1977, 15, 19.

    Google Scholar 

  5. E. Roberts, D. N. Krause, E. Wong, and A. Mori, J. Neurosci., 1981, 1, 132.

    Google Scholar 

  6. F. M. Vaz and R. J. A. Wanders, Biochem. J., 2002, 361, 417.

    Google Scholar 

  7. M. Tomita, Z. Physiol. Chem., 1923, 124, 253; (b) M. Hayashi, M. Tomita, and K. Nagai, Jpn. Pat. 33000772, 1958; Chem. Abstr., 1959, 53, 1172c-e.

    Google Scholar 

  8. S. P. A. Italseber, Fr. Pat. 4329, 1966; Chem. Abstr., 1967, 67, 100415.

    Google Scholar 

  9. Y. Fujimoto and S. Koshimoto, Jpn. Pat. 46008682, 1971; Chem. Abstr., 1971, 75, 36680.

    Google Scholar 

  10. S. A. Hebron, ES Pat. 391718, 1973; Chem. Abstr., 1974, 80, 47461.

    Google Scholar 

  11. M. Kurono, S. Shigeoka, S. Miyamoto, and K. Imaki, Jpn. Pat. 51039634, 1976; Chem. Abstr., 1976, 85, 62690.

    Google Scholar 

  12. M. Pinza and G. Pifferi, J. Pharm. Sci., 1978, 67, 120.

    Google Scholar 

  13. Jpn. Pat. 56068649, 1981; Chem. Abstr., 1981, 95, 169788.

  14. Jpn. Pat. 57183748, 1982; Chem. Abstr., 1983, 98, 106810.

  15. R. P. Jain and R. M. Williams, Tetrahedron Lett., 2001, 42, 4437; (b) G. Wang and R. I. Hollingsworth, Tetrahedron: Asymm., 1999, 10, 1895; (c) C. E. Song, J. K. Lee, I. O. Kim, and J. H. Choi, Synth. Commun., 1997, 27, 1009; (d) H. Sakagami, T. Kamikubo, and K. Ogasawara, Synlett, 1997, 2, 221; (e) B. B. Lohray, A. S. Reddy, and V. Bhushan, Tetrahedron: Asymm., 1996, 7, 2411.

    Google Scholar 

  16. R. P. Jain and R. M. Williams, Tetrahedron, 2001, 57, 6505; (b) O. Kanno, M. Miyauchi, and I. Kawamoto, Heterocycles, 2000, 53, 173; (c) A. B. Kazi, S. Shidmand, and J. Hajdu, J. Org. Chem., 1999, 64, 9337; (d) Y. Aoyagi and R. M. Williams, Tetrahedron, 1998, 54, 10419; (e) R. Leclerc and D. Uguen, Tetrahedron Lett., 1994, 35, 1999.

    Google Scholar 

  17. F. F. Fleming, Q. Wang, and O. W. Steward, J. Org. Chem., 2001, 66, 2171.

    Google Scholar 

  18. M. E. Jung and T. J. Shaw, J. Am. Chem. Soc., 1980, 102, 6304.

    Google Scholar 

  19. H. C. Kolb, Y. L. Bennani, and K. B. Sharpless, Tetrahedron: Asymm., 1993, 4, 133; (b) http://www.aist.go.jp/ RIODB/SDBS/menu-e.html; CAS Registry No. of (RS)-GABOB: 352-21-6.

    Google Scholar 

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Mete, E., Maraş, A. & Seçen, H. A short synthesis of 4-amino-3-hydroxybutyric acid (GABOB) via allyl cyanide. Russian Chemical Bulletin 52, 1879–1881 (2003). https://doi.org/10.1023/A:1026045829876

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