1258
NOVAKOV et al.
tanes), Volgograd: Volgogradskaya Meditsinskaya
4-(2-Amino)ethyladamantan-1-ol (2f) was prepared
Akademiya, 2001, p. 195.
similarly from 4.18 g (0.11 mol) of lithium aluminum
hydride and 10.7 g (0.052 mol) of (5-hydroxyadamant-
2-ylidene)acetonitrile 1f. Yield 7.3 g (0.037 mol,
72%), mp 63–64°С. IR spectrum, ν, cm–1: 668.1,
772.2, 810.0, 922.3, 1013.8, 1042.1, 1068.3, 1218.1,
1309.5, 1353.5, 1452.2, 1469.4, 1607.4, 1652.1, 2329.5,
2648.7, 2701.5, 2745.7, 2805.4, 2912.0, 3348.2, 3507.8,
2. US Patent 834459, 2007.
3. EP Patent 2439202А1, 2012, Spain.
4. Su, X., Vicker, N., Trusselle, M., Halem, H., Culler, M.D.,
and Potter, B.V.L., Mol. Cell. Endocrinology, 2009,
vol. 301, nos. 1–2, p. 169. DOI: 10.1016/j.mce.2008.08.006.
5. Gopalan, B., Ponpandian, T., Kachhadia, V., Bharathi-
mohan, K., Vignesh, R., Sivasudar, V., Narayanan, S.,
Mandar, B., Praveen, V., Saranya, N., Rajagopal, S.,
and Rajagopal, S., Bioorg. Med. Chem. Lett., 2013,
vol. 23, no. 9, p. 2532. DOI: 10.1016/j.bmcl.2013.03.002.
1
3678.2. Н NMR spectrum, δ, ppm (J, Hz): 0.89–0.94
m (3Н, NH2, CHAd), 1.15–1.16 m (2H, CH2CH2NH2),
1.33–1.53 m (16H, Ad), 2.02 s (1Н, OH), 2.28 d.t (2Н,
СН2СН2NH2, J = 7.1, 0.9). Mass spectrum (EI), m/e
(Irel, %):196.3 (6) [M]+, 195.3 (41) [M]+, 177 (14), 176
(100) [M –17]+, 162 (8), 161.1 (12), 133.2 (9).
6. Kolocouris, N., Foscolos, G.B., Kolocouris, A.,
Marakos, P., Pouli, N., Fytas, G., Ikeda, S., and De
Clercq, E., J. Med. Chem., 1994, vol. 37, p. 2896. DOI:
10.1021/jm00044a010.
4-(1-Aminoprop-2-yl)adamantan-1-ol (2g) was
prepared similarly from 4.35 g (0.11 mol)of lithium
aluminum hydride and 10.7 g (0.052 mol) of 2-(5-
hydroxyadamant-2-ylidene)propionitrile 1g. Yield 7.5 g
(0.036 mol, 70%), mp 36–37°С. IR spectrum, ν, cm–1:
810.0, 922.3, 965.3, 1054.6, 1091.7, 1151.7, 1303.3,
7. Kolocouris, N., Kolocouris, A., Foscolos, G.B., Fytas, G.,
Neyts, J., Padalko, E., Balzarini, J., Snoeck, R., Andrei, G.,
and De Clercq, E., J. Med. Chem., 1996, vol. 11,
p. 2025. DOI: 10.1021/jm950891z.
8. Seyden-Penne, J., Reductions by Alumino and
Borohydrides in Organic Synthesis, New York: Wiley-
VCH, 1997, p. 1.
1
1339.8, 1451.1, 1596.7, 1665.7, 2912.0, 3507.8. Н
NMR spectrum, δ, ppm (J, Hz): 0.83 d (3Н, СН3, J =
6.6), 0.85–2.08 m [19Н, NH2, CHAd, OH, СН(СН3)·
СН2NH2], 2.40 d.d [1Н, СН(СН3)СН2NH2, J = 12.6,
7.1], 2.75 d.d [1Н, СН(СН3)СН2NH2, J = 12.4, 3.0].
Mass spectrum (EI), m/e (Irel, %): 211.1 (11) [M]+,
210.2 (100), 209.3 (9), 192.3 (11), 191.3 (7), 190.4 (5).
9. Liu, S.X., Yang, Y.H., Zhen, X.L., Li, J.Z., He, H.M.,
Feng, J., and Whiting, A., Org. Biomol. Chem., 2012,
vol. 10, p. 663. DOI: 10.1039/c1ob06471a.
10. Laval, S., Dayoub, W., Favre-Reguillon, A., Berthod, M.,
Demonchaux, P., and Lemaire, M., Tetrahedron Lett.,
2009, vol. 50, p. 7005. DOI: 10.1016/j.tetlet.2009.09.164.
4-(1-Aminobut-2-yl)adamanatan-1-ol (2h) was
prepared similarly from 4.35 g (0.11 mol) of lithium
aluminum hydride and 11.3 g (0.052 mol) of 2-(5-
hydroxyadamant-2-ylidene)butanenitrile 1h. Yield
7.5 g (0.035 mol, 68%), mp 31–32°С. IR spectrum, ν,
cm–1: 811.0, 928.3, 961.3, 1054.6, 1091.7, 1154.7,
1303.3, 1339.8, 1451.1, 1596.7, 1665.7, 2912.0, 3515.8.
1Н NMR spectrum, δ, ppm (J, Hz): 0.82 d.t (3Н, СН3,
J = 7.1), 1.24–1.32 m [1H, СН(С2Н5)СН2NH2], 1.44–
1.84 m [17Н, NH2, СН(СH2CН3)СН2NH2], 2.1 s (1H,
OH), 2.75 d.d [2Н, СН(С2Н5)СН2NH2, J = 12.4, 3.0].
Mass spectrum (EI), m/e (Irel, %): 224.1 (15) [M]+,
223.2 (100), 194.2 (6), 192.3 (12), 177 (18), 134 (6),
133.2 (11).
11. Caddick, S., Judd, D.B., de Lewis, A.K.K., Reich, M.T.,
and Williams, M.R.V., Tetrahedron, 2003, vol. 59,
p. 5417. DOI: 10.1016/S0040-4020(03)00858-5.
12. Bornschein, Ch., Werkmeister, S., Wendt, B., Jiao, H.,
Alberico, E., Baumann, W., Junge, H., Junge, K., and
Beller, M., Nature Commun., 2014, vol. 5, Article
no. 4111. DOI: 10.1038/ncomms5111.
13. Haddenham, D., Pasumansky, L., De Soto, J., Eagon, S.,
and Singaram, B., J. Org. Chem., 2009, vol. 74, p. 1964.
DOI: 10.1021/jo8023329.
14. Popov, Yu.V., Mokhov, V.M., Tankabekyan, N.A., and
Uzakov, E.Yu., Izv. VolGTU, 2011, no. 2(75), p. 29.
15. Skomorokhov, M.Yu., Leonova, M.V., Shiryaev, A.K.,
and Klimochkin, Yu.N., Russ. J. Org. Chem., 2003, vol.
39, no. 9, p. 1360. DOI: 10.1023/B:RUJO.
0000010230.77371.3b.
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RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 6 2016