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5.2.4. N-Benzyl-3-methyl-2-(phenylselanyl)butan-1-
5.2.10. N-Benzyl-1-(phenylselanyl)propan-2-amine 6j.4a
Yield: 50%. 1H NMR d: 1.18 (d, 3H, JZ6.1 Hz, CH3), 1.80
(sl, 1H, NH), 2.85–3.09 (m, 3H, H-1, H-2), 3.70 (d, 1H, JZ
13.1 Hz, CH2Ph), 3.80 (d, 1H, JZ13.1 Hz, CH2Ph), 7.20–
7.35 (m, 8H, Ph), 7.45–7.49(m, 2H, Ph). 13C NMR d: 20.8
(C-3), 36.3 (C-1), 51.3 (CH2Ph), 51.7 (C-2), 127.0, 127.3,
128.2, 128.5, 129.2, 130.4, 133.0, 140.4 (Ph). Anal. Calcd
for C16H19NSe: C, 63.15; H, 6.30; N, 4.60. Found: C, 63.47;
H, 6.39; N, 4.27.
1
amine 6d.4a Yield: 69%. H NMR d: 1.01 (d, 3H, JZ
6.7 Hz, H-4), 1.05 (d, 3H, JZ6.7 Hz, H-4), 2.00–2.06 (m,
1H, H-3), 2.20 (sl, 1H, NH), 2.81 (dd, 1H, JZ8.4, 12.5 Hz,
H-1), 2.91 (dd, 1H, JZ5.1, 12.5 Hz, H-1), 3.24–3.29 (m,
1H, H-2), 3.70 (d, 1H, JZ13.4 Hz, CH2Ph), 3.75 (d, 1H, JZ
13.4 Hz, CH2Ph), 7.17–7.33 (m, 8H, Ph), 7.52–7.59 (m, 2H,
Ph). 13C NMR d: 20.1 (C-4), 21.0 (C-4), 31.2 (C-3), 51.7
(C-1), 53.6 (CH2Ph), 56.7 (C-2), 126.8, 127.1, 127.4, 128.0,
128.3, 128.9, 134.3, 140.2 (Ph). Anal. Calcd for C18H23NSe:
C, 65.05; H, 6.98; N, 4.21. Found: C, 64.86; H, 6.71, N,
4.49.
5.2.11. N-Benzyl-3,3-dimethyl-1-(phenylselanyl)butan-2-
amine 6k.4a Yield: 71%. 1H NMR d: 1.06 (s, 9H, C(CH3)3),
1.37 (sl, 1H, NH), 2.59 (dd, 1H, JZ9.0, 3.4 Hz, H-1), 3.00
(dd, 1H, JZ12.1, 9.0 Hz, H-2), 3.39 (dd, 1H, JZ12.1,
3.4 Hz, H-2), 3.85 (d, JZ12.4 Hz, CH2Ph), 4.06 (d, JZ
12.4 Hz, CH2Ph), 7.28–7.45 (m, 8H, Ph), 7.58–7.62 (m, 2H,
Ph). 13C NMR d: 27.1 (C-4), 32.3 (C-1), 36.4 (C-3), 55.4
(CH2Ph), 66.6 (C-2), 126.8, 127.3, 128.0, 128.4, 129.1,
130.0, 133.6, 141.1 (Ph). Anal. Calcd for C19H25NSe: C,
65.88; H, 7.28; N, 4.04. Found: C, 66.10; H, 7.31; N, 4.29.
5.2.5. N-Benzyl-2-(phenylselanyl)hexan-1-amine 6e.
Yield: 65%. 1H NMR d: 0.87 (t, 3H, JZ7.2 Hz, H-6),
1.22–1.55 (m, 4H, H5, H-4), 1.56–1.60 (m, 2H, H-3), 1.80
(sl, 1H, NH), 2.67 (dd, 1H, JZ7.9, 12.3 Hz, H-1), 2.77 (dd,
1H, JZ4.8, 12.3 Hz, H-1), 3.21–3.31(m, 1H, H-2), 3.74 (d,
1H, JZ13.4 Hz, CH2Ph), 3.81 (d, 1H, JZ13.4 Hz, CH2Ph),
7.21–7.34 (m, 8H, Ph), 7.47–7.51 (m, eH, Ph). 13C NMR d:
´
14.1 (C-6), 22.6 (C-5), 30.1 (C-4), 33.6 (C-3), 47.5 (C-2),
53.0 (C-1), 53.7 (CH2Ph), 127.0, 127.7, 128.2, 128.3, 128.5,
129.0, 135.4, 140.4 (Ph). Anal. Calcd for C19H25NSe: C,
65.88; H, 7.27; N, 4.04. Found: C, 66.14; H, 6.95; N, 4.27.
5.2.12. N-Benzyl-1-phenyl-2-(phenylselanyl)ethan-1-
1
amine 6l. Yield: 68%. 77Se NMR d: 268.5. H NMR d:
2.25(sl, 1H, NH), 3.06 (dd, 1H, JZ9.7, 12.3 Hz, H-2), 3.22
(dd, 1H, JZ4.3, 12.3 Hz, H-2), 3.49 (d, 1H, JZ13.4 Hz,
CH2Ph), 3.70 (d, 1H, JZ13.4 Hz, CH2Ph), 3.75 (dd, 1H,
JZ4.3, 9.7 Hz, H-1), 7.20–7.32 (m, 13H, Ph), 7.40–7.44 (m,
2H, Ph). 13C NMR d: 37.0 (C-2), 51.6 (CH2Ph), 61.1 (C-1),
127.0, 127.2, 127.3, 127.7, 128.3, 128.5, 128.8, 129.2,
129.8, 133.2, 140.4, 143.0 (Ph). Anal. Calcd for C21H21NSe:
C, 68.84; H, 5.78; N, 3.82. Found: C, 68.86; H, 5.96; N,
4.19.
5.2.6. N-Benzyl-3-phenyl-2-(phenylselanyl)propan-1-
amine 6f. Yield: 67%. 1H NMR d: 2.67–2.87 (m, 2H,
H-1), 2.94–3.14 (m, 2H, H-3), 3.50–3.65 (m, 1H, H-2), 3.71
(d, 1H, JZ13.5 Hz, CH2Ph), 3.81 (d, 1H, JZ13.5 Hz,
CH2Ph), 7.15–7.40 (m, 13H, Ph), 7.47–7.53 (m, 2H, Ph).
13C NMR d: 40.3 (C-3), 47.5 (C-2), 51.7, 53.5 (C-1,
CH2Ph), 126.9, 127.7, 128.2, 128.4, 129.0, 129.1, 135.3,
139.6 (Ph). Anal. Calcd for C22H23NSe: C, 69.46; H, 6.09;
N, 3.68. Found: C, 69.30; H, 6.12; N, 3.55.
5.2.13. N-Benzyl-2-(phenylselanyl)pentan-3-amine 6m.4a
Yield: 57%, syn/anti: 80/20. Diastereomer syn; 1H NMR d:
0.89 (t, 3H, JZ7.4 Hz, H-5), 1.41 (d, 3H, JZ7.1 Hz, H-1),
1.42–1.51 (m, 1H, H-4), 1.66–1.77 (m, 1H, H-4), 2.00 (sl,
1H, NH), 2.57 (dt, 1H, JZ4.9, 6.6 Hz, H-3), 3.46 (qd, 1H,
JZ4.9, 7.1 Hz, H-2), 3.74 (d, 1H, JZ13.3 Hz, CH2Ph), 3.79
(d, 1H, JZ13.3 Hz, CH2Ph), 7.15–7.32 (m, 8H, Ph), 7.50–
7.54 (m, 2H, Ph). 13C NMR d: 10.4 (C-5), 18.8 (C-1), 23.9
(C-4), 44.7 (C-2), 51.9 (CH2Ph), 62.7 (C-3), 127.0, 127.4
128.3, 128.5, 129.0, 129.4, 134.9, 140.2 (Ph). Diastereomer
anti; 1H NMR d: 0.88 (t, 3H, JZ7.4 Hz, H-5), 1.39 (d, 3H,
JZ7.1 Hz, H-1), 1.50–1.60 (m, 1H, H-4), 1.66–1.76 (m, 1H,
H-4), 2.00 (sl, 1H, NH), 2.52–2.59 (m, 1H, H-3), 3.60–3.65
(m, 1H, H-2), 3.88 (m, 2H, CH2Ph), 7.15–7.32 (m, 8H, Ph),
7.48–7.52 (m, 2H, Ph). 13C NMR d: 11.2 (C-5), 17.6 (C-1),
24.7 (C-4), 45.3 (C-2), 51.9 (CH2Ph), 62.7 (C-3), 127.8,
128.8, 129.0, 129.9, 130.2, 134.9, 135.3, 139.8 (Ph). Anal.
Calcd for C18H23NSe: C, 65.05; H, 6.98; N, 4.21. Found: C,
65.36; H, 6.81; N, 4.59.
5.2.7. N-Benzyl-2-methyl-2-(phenylselanyl)propan-1-
1
amine 6g.4a Yield: 64%. H NMR d: 1.40 (s, 6H, H-3),
1.84 (sl, 1H, NH), 2.50 (s, 2H, H-1), 3.86 (s, 2H, CH2Ph),
7.25–7.40 (m, 8H, Ph), 7.47–7.53 (m, 2H, Ph). 13C NMR d:
28.4 (C-3), 48.4 (C-2), 54.0 (CH2Ph), 59.2 (C-1), 126.8,
127.0, 127.6, 128.1, 128.3, 128.9, 134.2, 141.1 (Ph). Anal.
Calcd for C17H21NSe: C, 64.14; H, 6.65; N, 4.40. Found: C,
64.45; H, 6.79; N, 4.19.
5.2.8. N-Benzyl-2-phenyl-2-(phenylselanyl)propan-1-
1
amine 6h. Yield: 59%. 77Se NMR d: 564.8. H NMR d:
1.50 (sl, 1H, NH), 1.84 (s, 3H, H-3), 3.00 (d, 1H, JZ
12.0 Hz, H-1), 3.25 (d, 1H, JZ12.0 Hz, H-1), 3.79 (s, 2H,
CH2Ph), 7.10–7.35 (m, 15H, Ph). 13C NMR d: 26.0 (C-3),
52.7 (C-2), 54.2 (CH2Ph), 58.7 (C-1), 126.8, 127.0, 127.4,
127.8, 128.2, 128.3, 128.5, 128.6, 128.7, 137.9, 140.5, 144.1
(Ph). Anal. Calcd for C22H23NSe: C, 69.46; H, 6.09; N,
3.68. Found: C, 69.26; H, 5.86; N, 3.98.
5.2.14. syn-N-Benzyl-1-phenyl-2-(phenylselanyl)propan-
1
1-amine 6n.4a Yield: 53%. H NMR d: 1.30 (d, 3H, JZ
5.2.9. Phenyl-N-((1-(phenylselanyl)cyclohexyl)methyl)
methanamine 6i. Yield: 51%. H NMR d: 0.90–1.90 (m,
7.1 Hz, H-3), 2.20 (sl, 1H, NH), 3.47 (d, 1H, JZ13.3 Hz,
CH2Ph), 3.61 (qd, 1H, JZ3.5, 7.1 Hz, H-2), 3.76 (d, 1H, JZ
13.3 Hz, CH2Ph), 3.83 (d, 1H, JZ3.4 Hz, H-1), 7.20–7.40
(m, 13H, Ph), 7.46–7.50 (m, 2H, Ph). 13C NMR d: 15.7
(C-3), 47.3 (C-2), 51.7 (CH2Ph), 64.3 (C-1), 127.0, 127.4,
127.7, 128.0, 128.3, 128.4, 129.2, 129.4, 129.6, 135.0,
140.5, 141.0 (Ph). Anal. Calcd for C22H23NSe: C, 69.47; H,
6.09; N, 3.68. Found: C, 69.82; H, 6.31; N, 3.49.
1
11H, Cy, NH), 2.47–2.52 (m, 2H, H-1), 3.81 (s, 2H,
CH2Ph), 7.20–7.45 (m, 8H, Ph), 7.57–7.64 (m, 2H, Ph). 13
C
NMR d: 26.1, 31.4, 35.5, 53.2, 54.0 56.1 (C-1, CH2Ph),
126.7, 128.0, 128.2, 128.5, 129.0, 131.3, 137.9, 140.4 (Ph).
Anal. Calcd for C20H25NSe: C, 67.02; H, 7.03; N, 3.91.
Found: C, 66.73; H, 6.86; N, 3.78.