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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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.
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.
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.
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.
E. Roberts, D. N. Krause, E. Wong, and A. Mori, J. Neurosci., 1981, 1, 132.
F. M. Vaz and R. J. A. Wanders, Biochem. J., 2002, 361, 417.
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.
S. P. A. Italseber, Fr. Pat. 4329, 1966; Chem. Abstr., 1967, 67, 100415.
Y. Fujimoto and S. Koshimoto, Jpn. Pat. 46008682, 1971; Chem. Abstr., 1971, 75, 36680.
S. A. Hebron, ES Pat. 391718, 1973; Chem. Abstr., 1974, 80, 47461.
M. Kurono, S. Shigeoka, S. Miyamoto, and K. Imaki, Jpn. Pat. 51039634, 1976; Chem. Abstr., 1976, 85, 62690.
M. Pinza and G. Pifferi, J. Pharm. Sci., 1978, 67, 120.
Jpn. Pat. 56068649, 1981; Chem. Abstr., 1981, 95, 169788.
Jpn. Pat. 57183748, 1982; Chem. Abstr., 1983, 98, 106810.
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.
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.
F. F. Fleming, Q. Wang, and O. W. Steward, J. Org. Chem., 2001, 66, 2171.
M. E. Jung and T. J. Shaw, J. Am. Chem. Soc., 1980, 102, 6304.
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.
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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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DOI: https://doi.org/10.1023/A:1026045829876