The Journal of Organic Chemistry
Article
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18: 1H NMR (600 MHz, CDCl3) δ = 1.40 (br 1H, NH), 1.42 (d J =
6.6 Hz, 3H, H-13), 1.62 (m, 1H, H-3β), 2.16 (m, 1H, H-3α), 2.24 (s,
3H, H-11), 2.59 (m, 1H, H-4β), 2.62 (m, 1H, H-1α), 2.79 (m, 1H, H-
2), 2.80 (m, 1H, H-1β), 2.92 (dt J1 = 17.7 Hz, J2 = 10.4, J3 = 5.1 Hz,
1H, H-4α), 4.05 (q J = 6.6 Hz, 1H, H-12), 6.78 (s, 1H, H-8), 7.21 (s,
1H, H-6), 7.26−7.37 (m, 5H, Ph-ring) ppm; 13C NMR (100 MHz,
CDCl3) δ = 20.5 (C-11), 24.9 (C-13), 28.6 (C-4), 28.9 (C-3), 37.9
(C-1), 50.0 (C-2), 55.0 (C-12), 136.7 (C-7), 130.6 (C-6), 129.3 (C-8),
132.5 (C-10), 137.4 (C-9), 138.5 (C-5), 126.5, 126.9, 128.5, 145.8
(Ph-ring) ppm; HRMS data were recorded using ESI positive
ionization mode calcd for C19H23BrN 344.1014; m/z M + 1, 344.1013.
24: H NMR (600 MHz, CDCl3) δ = 1.33 (d J = 6.6 Hz, 3H, H-
13), 1.40 (br 1H, NH), 1.54 (m, 1H, H-3β), 2.08 (m, 1H, H-3α), 2.21
(s, 3H, H-11), 2.48 (m, 1H, H-1α), 2.51 (m, 1H, H-4α), 2.71 (m, 1H,
H-2), 2.72 (m, 1H, H-1β), 2.74 (m, 1H, H-4β), 3.98 (q J = 6.6 H-12),
6.62 (d J = 8.4 H-8), 7.20 (d J = 8.4 H-7), 7.26−7.37 (m, 5H, Ph-ring)
ppm; 13C NMR (100 MHz, CDCl3) δ = 19.0 (C-11), 24.6 (C-13),
26.8 (C-4), 29.7 (C-3), 36.6 (C-1), 49.8 (C-2), 55.0 (C-12), 122.7 (C-
6), 128.2 (C-8), 129.8 (C-7), 134.6 (C-10), 135.5 (C-5), 136.4 (C-9),
126.5, 126.9, 128.5, 145.9 (Ph-ring) ppm; HRMS data were recorded
using ESI positive ionization mode calcd for C19H23BrN 344.1014; m/
z M + 1, 344.1016.
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19: H NMR (400 MHz, CDCl3) δ = 1.39 (d J = 6.6 Hz, 3H, H-
13), 1.40 (br 1H, NH),1.52 (m, 1H, H-3β), 1.84 (m, 1H, H-3α), 2.36
(s, 3H, H-11), 2.48 (dd J1 = 17.0 Hz, J2 = 9.0 Hz, 1H, H-1α), 2.69 (ddd
J1 = 16.2 Hz, J2 = 10.8 Hz, J3 = 5.4 Hz, 1H, H-4α), 2.75 (m, 2H, H-2,
H-4β), 3.19 (dd J1 = 16.9 Hz, J2 = 5.2 Hz, 1H, H-1β), 4.08 (q J = 6.6
Hz, 1H, H-12), 6.89 (d J = 6.6 Hz, 1H, H-5), 6.97 (d J = 6.6 Hz, 1H,
H-6), 7.26−7.37 (m, 5H, Ph-ring) ppm; 13C NMR (100 MHz,
CDCl3) δ = 23.6 (C-11), 24.9 (C-13), 28.5 (C-4), 29.9 (C-3), 38.0
(C-1), 51.0 (C-2), 55.1 (C-12), 127.3 (C-5), 127.8 (C-6), 128.2 (C-8),
128.5 (C-7), 135.5 (C-10), 136.1 (C-9), 126.5, 127.0, 128.5, 145.4
(Ph-ring) ppm; HRMS data were recorded using ESI positive
ionization mode calcd for C19H23BrN 344.1014; m/z M + 1, 344.1016.
ASSOCIATED CONTENT
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S
* Supporting Information
Proton and carbon NMR spectra of novel reported compounds
13−24 as well as the associated high-resolution mass spectra
(HRMS). This material is available free of charge via the
AUTHOR INFORMATION
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Corresponding Author
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20: H NMR (400 MHz, CDCl3) δ = 1.40 (d J = 6.0 Hz, 3H, H-
13), 1.40 (br 1H, NH),1.49 (m, 1H, H-3β), 2.07 (m, 1H, H-3α), 2.34
(s, 1H, H-11), 2.45 (dd J1 = 16.6 Hz, J2 = 7.8 Hz, 1H, H-1α), 2.67 (m,
1H, H-4 α), 2.77 (m, 1H, H-2), 2.84 (dt J1 = 16.7 Hz, J2 = 4.8 Hz, 1H,
H-4β), 2.99 (dd J1 = 17.0 Hz, J2 = 4.6 Hz, 1H, H-1β), 4.06 (q J = 6.5
Hz, 1H, H-12), 6.89 (d J = 7.7 Hz, 1H, H-5), 6.96 (d J = 7.7 Hz, 1H,
H-6), 7.26−7.37 (m, 5H, Ph-ring) ppm; 13C NMR (100 MHz,
CDCl3) δ = 23.6 (C-11), 25.0 (C-13), 28.2 (C-3), 28.4 (C-4), 39.1
(C-1), 50.8 (C-2), 54.8 (C-12), 127.2 (C-5), 127.8 (C-6), 128.2 (C-8),
135.5 (C-7), 136.0 (C-10), 136.9 (C-9), 126.5, 127.0, 128.5, 145.4
(Ph-ring) ppm; HRMS data were recorded using ESI positive
ionization mode calcd for C19H23BrN 344.1014; m/z M + 1, 344.1017.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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The skilled support provided by our AstraZeneca colleagues in
the Analytical Science Department, Egil Forsberg, Margareta
Andersson, and Dr Hefeng Pan, as well as Dr Susanne Olofsson
in the Neuroscience Medicinal Chemistry unit, Sodertalje,
during the course of this investigation is gratefully acknowl-
edged.
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21: H NMR (600 MHz, CDCl3) δ = 1.36 (d J = 6.6 Hz, 3H, H-
13), 1.40 (br 1H, NH), 1.54 (m, 1H, H-3β), 1.84 (m, 1H, H-3α), 2.29
(s, 3H, H-11), 2.48 (dd J1 = 16.1 Hz, J2 = 8.9 Hz, 1H, H-1α), 2.64 (ddd
J1 = 16.8 Hz, J2 = 10.8 Hz, J3 = 6.0 Hz, 1H, H-4α), 2.74 (m, 2H, H-2,
H-4β), 2.93 (dd J1 = 16.1 Hz, J2 = 4.7 Hz, 1H, H-1β), 4.00 (q J = 6.6
Hz, 1H, H-12), 6.91 (s, 1H, H-8), 7.19 (s, 1H, H-5), 7.26−7.37 (m,
5H, Ph-ring) ppm; 13C NMR (100 MHz, CDCl3) δ = 22.3 (C-11),
25.0 (C-13), 27.3 (C-4), 30.2 (C-3), 35.9 (C-1), 50.3 (C-2), 54.9 (C-
12), 121.7 (C-6), 128.5 (C-7), 131.5 (C-8), 132.0 (C-5), 134.7 (C-9),
135.7 (C-10), 126.5, 127.0, 128.5, 145.4 (Ph-ring) ppm; HRMS data
were recorded using ESI positive ionization mode calcd for C19H23BrN
344.1014; m/z M + 1, 344.1015
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1
22: H NMR (600 MHz, CDCl3) δ = 1.36 (d J = 6.6 Hz, 3H, H-
13), 1.40 (br 1H, NH), 1.51 (m, 1H, H-3β), 2.05 (m, 1H, H-3α), 2.28
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(Ph-ring) ppm; HRMS data were recorded using ESI positive
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