ARYLATION OF ADAMANTANAMINES: IX.
1797
3
8. Ostheimer, K.E., Busch, T., Gortelmeyer, R., and
spectrum, δ, ppm: 0.93 d (3H, J = 6.6 Hz), 1.18–
1.40 m (3H), 1.59–1.97 m (10H), 2.03 s (1H), 2.07 s
(1H), 2.12 s (1H), 2.72–2.80 m (1H), 3.24 d.d (1H,
2J = 12.4, 3J = 3.0 Hz), 4.23 br.s (1H), 6.54 d (2H, 3J =
8.6 Hz), 7.32 d (2H, 3J = 8.6 Hz). 13C NMR spectrum,
δC, ppm: 16.0, 30.0, 30.1, 30.6, 31.3 (2C), 31.6, 45.4,
46.0, 46.2 (2C), 47.4, 67.4, 111.3 (2C), 126.3 (2C),
150.9; two quaternary carbon signals were not
identified. Mass spectrum: m/z 354.208 [M + H]+.
C20H27F3NO. Calculated: M + H 354.204.
Hahn, K.D., Arzneim. Forsch., 1989, vol. 39, p. 1152.
9. Boudakian, M.M., Fluorinated Aromatic Compounds.
Kirk-Othmer Encyclopedia of Chemical Technology,
Wiley, 2000, p. 56.
10. Scherman, M.S., North, E.J., Jones, V., Hess, T.N.,
Grzegorzwicz, A.E., Kasagami, T., Kim, I.-H., Merzli-
kin, O., Lenaerts, A.J., Lee, R.E., Jackson, M.,
Morisseau, C., and McNeil, M.R., Bioorg. Med. Chem.,
2012, vol. 20, p. 3255.
11. Al-Omar, M.A., Al-Abdullah, E.S., Shehata, I.A.,
Habib, E.E., Ibrahim, T.M., and El-Emam, A.A.,
Molecules, 2010, vol. 15, p. 2526.
12. Yu, X., Zhang, M., Annamalai, T., Bansod, P.,
Narula, G., Tse-Dinh, Y.-C., and Sun, D., Eur. J. Med.
Chem., 2017, vol. 125, p. 515.
4-[1-(4-Methoxyanilino)propan-2-yl]adamantan-
1-ol (58) was synthesized from 105 mg of amino
alcohol 14 and 146 mg of 1-iodo-4-methoxybenzene.
Yield 80 mg (51%). 1H NMR spectrum, δ, ppm: 0.96 d
3
(3H, J = 6.6 Hz), 1.20–1.41 m (3H), 1.55–1.96 m
(10H), 2.05 s (1H), 2.10 s (1H), 2.16 s (1H), 2.70–
2.80 m (1H), 3.21 br.d (1H, 2J = 14.9 Hz), 3.74 s (3H),
6.54 d (2H, 3J = 8.3 Hz), 6.75 d (2H, 3J = 8.3 Hz); NH
proton signal was not identified. 13C NMR spectrum, δ,
ppm: 16.1, 30.0, 30.1, 30.5, 31.2, 31.3, 31.4, 45.4,
46.1, 46.2 (2C), 48.9, 55.6, 67.6, 114.7 (2C), 116.2
(2C), 142.7, 151.6. Mass spectrum: m/z 316.237
[M+H]+. C20H30NO2. Calculated M + H 316.228.
13. O’Brien-Brown, J., Jackson, A., Reekie, T.A.,
Barron, M.L., Werry, E.L., Schiavini, P., McDon-
nell, M., Munoz, L., Wilkinson, S., Noll, B., Wang, S.,
and Kassiou, M., Eur. J. Med. Chem., 2017, vol. 130,
p. 433.
14. Udagawa, S., Sakami, S., Takemura, T., Sato, M.,
Arai, T., Nitta, A., Aoki, T., Kawai, K., Iwamura, T.,
Okazaki, S., Takahashi, T., and Kaino, M., Bioorg. Med.
Chem. Lett., 2013, vol. 23, p. 1617.
This study was performed under financial support
by the Russian Foundation for Basic Research (project
nos. 16-03-00 349, 17-03-00 888; synthesis of
adamantane-containing amines) and by the Russian
Science Foundation (project no. 14-23-00186P; study
of catalytic transformations).
15. Rohde, J.J., Pliushchev, M.A., Sorensen, B.K.,
Wodka, D., Shuai, Q., Wang, J., Fung, S.,
Monzon, K.M., Chiou, W.J., Pan, L., Deng, X.,
Chovan, L.E., Ramaiya, A., Mullally, M., Henry, R.F.,
Stolarik, D.F., Imade, H.M., Marsh, K.C.,
Beno, D.W.A., Fey, T.A., Droz, B.A., Brune, M.E.,
Camp, H.S., Sham, H.L., Frevert, E.U., Jacobson, P.B.,
and Link, J.T., J. Med. Chem., 2007, vol. 50, p. 149.
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 53 No. 12 2017