DVORNIKOVA et al.
490
CH3, t-Bu), 1.57 d (1H, 7β-H, J = 10.3 Hz), 1.87 t (1H,
1-H, J = 5.5 Hz), 1.94 m (1H, 5-H), 2.09–2.16 m (1H,
7α-H), 2.26–2.36 m (1H, 4α-H), 2.82–2.98 m (4H,
11-H, 12-H), 3.10 br.t (1H, 3-H), 3.98 m (2H,
NHCH2Ar), 6.88 m (1H, Harom), 7.24 m (1H, Harom).
13C NMR spectrum, δC, ppm: 23.10 (C9), 24.72 (C7),
24.76 (C8), 27.66 (C10), 29.64 and 31.68 [C(CH3)3],
33.24 (C4), 34.11 and 34.88 [C(CH3)3], 39.13 (C6),
40.28 (C5), 47.58 and 48.72 (C11, C12), 53.29
(NHCH2Ar), 55.72 (C1), 60.64 (C3), 77.74 (C2), 122.20
(Carom), 122.87, 123.06 (CHarom), 135.88, 140.31 (Carom),
154.75 (C2′). Found, %: C 75.14; H 10.86; N 6.39.
C27H46N2O2. Calculated, %: C 75.30; H 10.77; N 6.50.
(1H, 2′-H, J = 9.0 Hz), 3.95 m (2H, NHCH2Ar), 6.65 s
(1H, Harom), 7.02 s (1H, Harom). 13C NMR spectrum, δC,
ppm: 12.22, 20.37 (CH3); 20.89 (5″-CH3); 21.47, 23.12
(CH3); 24.71 (C7), 24.76 (CH3), 27.54 (C5′), 27.67
(CH3), 33.09 (C4), 33.90 (C3′), 39.14 (C6), 39.61 (C6′),
40.28 (C5), 44.71 (C2′), 45.78 (C4′), 47.88 (C1′), 47.39
and 48.32 (C11, C12), 49.78 (C7′), 52.48 (NHCH2Ar),
55.67 (C1), 60.69 (C3), 76.64 (C2), 121.55 (Carom),
126.17 (CHarom), 126.54 (Carom), 127.78 (CHarom),
130.68 (Carom), 154.95 (C2″). Found, %: C 77.00;
H 10.35; N 5.92. C30H48N2O2. Calculated, %: C 76.87;
H 10.32; N 5.98.
(1R,2R,3R,5R)-3-[2-(2-Hydroxy-5-methyl-3-
{(1S,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl}-
benzylamino)ethylamino]-2,6,6-trimethylbicyclo-
[3.1.1]heptan-2-ol (11h). Yield 69% [calculated on
(–)-4b], colorless vitreous solid, [α]D = –19.5° (c = 2.0,
CHCl3). IR spectrum (KBr), ν, cm–1: 3415, 3309, 2947,
1606, 1463, 1381, 1369, 1226, 1116, 864, 756. 1H NMR
spectrum, δ, ppm: 0.77 s (3H, CH3), 0.83 s (3H, CH3),
0.88 s (3H, CH3), 0.90 s (3H, CH3), 1.24 s (3H, CH3),
1.29–1.48 m (2H, 4-H, 5′-H), 1.36 s (3H, CH3), 1.49–
1.68 m (4H, 7β-H, 3′-H, 6′-H), 1.74–1.97 m (4H, 1-H,
4′-H, 5-H, 5′-H), 2.09–2.18 m (2H, 3′-H, 7α-H), 2.24 s
(3H, 5″-CH3), 2.24–2.34 m (1H, 4-H), 2.72–2.98 m
(4H, 11-H, 12-H), 3.11 t (1H, 3-H, J = 9.0 Hz), 3.28 t
(1H, 2′-H, J = 9.0 Hz), 3.91 d and 4.00 d (1H each,
13-H, J = 13.6 Hz), 6.65 s (1H, Harom), 7.02 s (1H,
Harom). 13C NMR spectrum, δC, ppm: 12.23, 20.24
(CH3); 20.90 (5″-CH3); 21.47, 23.11 (CH3); 24.71 (C7),
24.79 (CH3), 27.55 (C5′), 27.66 (CH3), 32.88 (C4),
33.97 (C3′), 39.16 (C6), 39.64 (C6′), 40.24 (C5), 44.71
(C2′), 45.76 (C4′), 47.88 (C1′), 47.34 and 48.11 (C11,
C12), 49.76 (C7′), 52.47 (NHCH2Ar), 55.68 (C1), 60.73
(C3), 77.60 (C2), 121.42 (Carom), 126.26 (CHarom),
126.59 (Carom), 127.83 (CHarom), 130.72 (Carom), 154.91
(C2″). Found, %: C 76.98; H 10.23; N 5.85.
C30H48N2O2. Calculated, %: C 76.87; H 10.32; N 5.98.
(1R,2R,3R,5R)-3-[2-(3-tert-Butyl-5-methyl-2-hy-
droxybenzylamino)ethylamino]-2,6,6-trimethyl-
bicyclo[3.1.1]heptan-2-ol (11f). Yield 76% [calculated
on (–)-2], light brown thick oily material, [α]D =
–21.3° (c = 0.9, CHCl3). IR spectrum (film), ν, cm–1:
3431, 3307, 2912, 1604, 1465, 1444, 1386, 1359,
1
1240, 1143, 1111, 862, 758. H NMR spectrum, δ,
ppm: 0.88 s (3H, CH3), 1.24 s (3H, CH3), 1.35 s (3H,
CH3), 1.35–1.48 m (1H, 4β-H), 1.41 s (9H, t-Bu),
1.57 d (1H, 7β-H, J = 10.3 Hz), 1.87 t (1H, 1-H, J =
5.6 Hz), 1.94 m (1H, 5-H), 2.09–2.16 m (1H, 7α-H),
2.24 (3H, 5′-CH3), 2.24–2.35 m (1H, 4α-H), 2.77–
2.98 m (4H, 11-H, 12-H), 3.11 t (1H, 3-H, J = 9.0 Hz),
3.95 m (2H, NHCH2Ar), 6.70 s (1H, Harom), 6.99 s
(1H, Harom). 13C NMR spectrum, δC, ppm: 20.74
(5′-CH3), 23.08 (C9), 24.72 (C7), 24.77 (C8), 27.66
(C10), 29.59 [C(CH3)3], 33.08 (C4), 34.57 [C(CH3)3],
39.15 (C6), 40.27 (C5), 47.47 and 48.40 (C11, C12),
52.79 (NHCH2Ar), 55.76 (C1), 60.68 (C3), 77.68 (C2),
122.82 (Carom), 126.52, 126.93 (CHarom), 127.61
(Carom), 136.57 (Carom), 154.84 (C2′). Found, %:
C 74.02; H 10.47; N 7.10. C24H40N2O2. Calculated, %:
C 74.18; H 10.38; N 7.21.
(1R,2R,3R,5R)-3-[2-(2-Hydroxy-5-methyl-
3-{(1R,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-
yl}benzylamino)ethylamino]-2,6,6-trimethylbicyclo-
[3.1.1]heptan-2-ol (11g). Yield 83% [calculated on
(–)-4b], colorless vitreous solid, [α]D = –23.9° (c = 1.1,
CHCl3). IR spectrum (KBr), ν, cm–1: 3441, 3307, 2947,
(1R,2R,3R,5R)-3-[2-(2-Hydroxy-5-methyl-3-
{(1R,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl}-
benzylamino)ethylamino]-2,6,6-trimethylbicyclo-
[3.1.1]heptan-2-ol (11i). Yield 68% [calculated on
(–)-2], colorless vitreous solid, [α]D = +28.0° (c = 0.4,
CHCl3). IR spectrum (KBr), ν, cm–1: 3396, 3273, 2949,
1602, 1560, 1467, 1408, 1390, 1222, 1155, 756.
1H NMR spectrum, δ, ppm: 0.74 s (3H, CH3), 0.92 s
(3H, CH3), 1.06 s (3H, CH3), 1.11–1.21 m (1H, 4-H),
1.25 s (3H, CH3), 1.32–1.41 m (2H, 5′-H, 6′-H), 1.47 s
(3H, CH3), 1.52–1.59 m (1H, 4-H), 1.57 d (1H, 7β-H,
J = 10.6 Hz), 1.64–2.01 m (5H, 1-H, 3′-H, 4′-H, 5-H,
1
1606, 1463, 1382, 1369, 1226, 1120, 756. H NMR
spectrum, δ, ppm: 0.78 s (3H, CH3), 0.83 s (3H, CH3),
0.88 s (3H, CH3), 0.90 s (3H, CH3), 1.24 s (3H, CH3),
1.30–1.43 m (2H, 4-H, 5′-H), 1.34 s (3H, CH3), 1.48–
1.63 m (4H, 3′-H, 6′-H, 7β-H), 1.81–1.97 m (4H, 1-H,
4′-H, 5-H, 5′-H), 1.91–1.97 m (2H, 3′-H, 7α-H), 2.24 s
(3H, 5″-CH3), 2.24–2.34 m (1H, 4-H), 2.74–2.97 m
(4H, 11-H, 12-H), 3.09 t (1H, 3-H, J = 9.0 Hz), 3.29 t
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 51 No. 4 2015