5134
B. Zeng et al. / Tetrahedron 63 (2007) 5129–5136
ꢁ
25
1
Mp 128–130 C. [a]D +109.1 (c 0.21, CHCl ). H NMR
3
4.2.1.10. (1S,2S,3aS,6aS)-2-(Benzhydrylcarbamoyl)-
1-((1-oxidopyridin-2-yl)methyl)-octahydrocyclopenta[b]-
pyrrole 1-oxide (1h). The title compound 1h was obtained
by silica gel column chromatography (ethyl acetate/meth-
anol¼5:1, v/v) as a white solid in 86% yield. Mp 80–
(
400 MHz, CDCl ): d¼13.46 (s, 1H), 8.26 (d, J¼7.2 Hz,
3
2
1
4
H), 7.94–7.92 (m, 1H), 7.30–7.27 (m, 2H), 7.10–7.06 (m,
H), 6.97–6.89 (m, 2H), 5.13 (d, J¼11.6 Hz, 1H), 4.63–
.56 (m, 2H), 4.18–4.14 (m, 1H), 3.94 (s, 3H), 2.75–2.71
ꢁ
83 C. [a] +88.4 (c 0.22, CHCl ). H NMR (400 MHz,
D 3
25
1
(
m, 1H), 2.66–2.59 (m, 1H), 2.36–2.29 (m, 1H), 1.97–
1
1
1
1
2
3
.86 (m, 2H), 1.73–1.69 (m, 1H), 1.55–1.47 (m, 2H), 1.28–
.25 (m, 1H) ppm; C NMR (100 MHz, CDCl ): d¼165.3,
CDCl ): d¼12.32 (d, J¼8.2 Hz, 1H), 8.24 (d, J¼6.4 Hz,
3
1
3
1H), 7.46–7.15 (m, 13H), 6.34 (d, J¼8.8 Hz, 1H), 5.02 (d,
J¼11.6 Hz, 1H), 4.65–4.61 (m, 1H), 4.16–4.09 (m, 2H),
2.75–2.68 (m, 1H), 2.61–2.54 (m, 1H), 2.32–2.19 (m, 1H),
1.85–1.83 (m, 2H), 1.73–1.66 (m, 1H), 1.56–1.43 (m, 2H),
3
49.8, 141.8, 139.2, 132.3, 127.3, 126.6, 125.0, 124.4, 121.8,
20.7, 110.2, 83.9, 80.4, 62.9, 55.9, 42.3, 34.4, 32.8, 28.2,
4.5 ppm. HRMS (ESI) calcd for C H N O [M+H] :
+
2
1 25 3 4
1
3
84.1918, found 384.4488.
1.29–1.23 (m, 1H) ppm; C NMR (100 MHz, CDCl3):
d¼166.4, 142.6, 141.6, 141.5, 139.3, 132.0, 128.8, 128.6,
127.6, 127.4, 127.1, 126.9, 126.8, 125.5, 84.0, 80.1, 63.0,
56.2, 42.3, 34.4, 32.8, 28.0, 24.7 ppm. HRMS (ESI) calcd
4
.2.1.7. (1S,2S,3aS,6aS)-2-Adancarbamoyl-1-((1-oxi-
dopyridin-2-yl)methyl)-octahydrocyclopenta[b]pyrrole
-oxide (1e). The title compound 1e was obtained by silica
+
1
for C H N O [M+H] : 444.2282, found 444.4870.
7 29 3 3
2
gel column chromatography (ethyl acetate/methanol¼5:1,
ꢁ
72.7 (c 0.44, CHCl3). H NMR (400 MHz, CDCl3):
25
D
v/v) as a white solid in 87% yield. Mp 67–69 C. [a]
+
4.2.1.11.
(1S,2S,3aS,6aS)-1-((1-Oxidopyridin-2-yl)-
1
methyl)-2-((S)-1-phenylethylcarbamoyl)-octahydrocyclo-
penta[b]pyrrole 1-oxide (1i). The title compound 1i
was obtained by silica gel column chromatography (ethyl
acetate/methanol¼5:1, v/v) as a white solid in 81% yield.
d¼10.55 (s, 1H), 8.32 (d, J¼5.2 Hz, 1H), 7.85–7.83 (m,
1
4
2
1
2
1
3
H), 7.37–7.33 (m, 2H), 5.12 (d, J¼12.0 Hz, 1H), 4.60–
.54 (m, 2H), 4.20–4.15 (m, 1H), 2.69–2.65 (m, 1H),
.55–2.50 (m, 1H), 2.15–2.01 (m, 10H), 1.88–1.84 (m,
H), 1.68 (s, 7H), 1.54–1.45 (m, 2H), 1.35–1.26 (m,
ꢁ
25
D
1
Mp 47–49 C. [a] +109.1 (c 0.23, CHCl ). H NMR
3
(400 MHz, CDCl ): d¼11.64 (d, J¼8.4 Hz, 1H), 8.21 (d,
3
1
3
H) ppm; C NMR (100 MHz, CDCl ): d¼165.8, 141.6,
J¼6.4 Hz, 1H), 7.46–7.42 (m, 3H), 7.34 (t, J¼7.6 Hz, 2H),
7.26–7.22 (m, 2H), 7.17 (t, J¼7.6 Hz, 1H), 5.21–5.16 (m,
1H), 4.94 (d, J¼12 Hz, 1H), 4.61–4.55 (m, 1H), 4.13–4.08
(m, 1H), 4.00 (dd, J¼5.6, 5.2 Hz, 1H), 2.72–2.66 (m, 1H),
3
39.5, 129.4, 126.9, 125.7, 83.8, 80.1, 62.8, 41.8, 41.6,
6.3, 34.3, 32.8, 27.9, 24.8 ppm. HRMS (ESI) calcd for
+
C H N O [M+H] : 412.2595, found 412.2600.
4 33 3 3
2
2
.66–2.53 (m, 1H), 2.26–2.15 (m, 1H), 1.88–1.81 (m, 2H),
4.2.1.8. (1S,2S,3aS,6aS)-2-(Cyclohexylcarbamoyl)-1-
(1-oxidopyridin-2-yl)methyl)-octahydrocyclopenta[b]-
1.73–1.67 (m, 1H), 1.56–1.43 (m, 5H), 1.28–1.21 (m,
1H) ppm; C NMR (100 MHz, CDCl ): d¼166.3, 144.0,
1
3
(
3
pyrrole 1-oxide (1f). The title compound 1f was obtained by
silica gel column chromatography (ethyl acetate/methanol¼
141.5, 139.2, 132.0, 128.7, 127.2, 126.7, 126.3, 125.2,
83.7, 80.0, 62.9, 48.5, 42.2, 34.4, 32.8, 28.0, 24.6,
22.6 ppm. HRMS (ESI) calcd for C H N O [M+H] :
ꢁ
25
D
+
5
+
:1, v/v) as a white solid in 77% yield. Mp 124–126 C. [a]
22 27 3 3
1
100.5 (c 0.21, CHCl3). H NMR (400 MHz, CDCl3):
382.2125, found 382.4760.
d¼10.87 (s, 1H), 8.23 (d, J¼6.0 Hz, 1H), 7.75–7.73 (m,
1
4
5
1
H), 7.29–7.24 (m, 2H), 5.01 (d, J¼12.0 Hz, 1H), 4.53–
.48 (m, 1H), 4.34 (d, J¼12 Hz, 1H), 3.98 (dd, J¼4.8,
.2 Hz, 1H), 3.76 (s, 1H), 2.61 (d, J¼7.2 Hz, 1H), 2.46 (s,
H), 2.08–2.05 (m, 1H), 1.80 (d, J¼12 Hz, 4H), 1.62–1.18
4.2.1.12. (1S,2S,3aS,6aS)-2-(Benzhydrylcarbamoyl)-
1-(pyridin-2-ylmethyl)-octahydrocyclopenta[b]pyrrole
1-oxide (2a). The title compound 2a was obtained by silica
gel column chromatography (ethyl acetate) as a white solid
1
3
ꢁ
25
(
1
4
m, 12H) ppm; C NMR (100 MHz, CDCl ): d¼165.2,
in 53% yield. Mp 45–47 C. [a] +21.1 (c 0.26, CHCl3).
3
D
1
40.6, 138.4, 128.8, 125.8, 124.5, 82.7, 78.9, 62.0, 46.4,
1.0, 33.5, 31.9, 31.7, 31.5, 27.0, 24.5, 23.6, 23.5 ppm.
HRMS (ESI) calcd for C H N O [M+H] : 360.2282,
2
H NMR (400 MHz, CDCl ): d¼12.50 (d, J¼8.9 Hz, 1H),
3
8.57 (d, J¼5.0 Hz, 1H), 7.66–7.61 (m, 1H), 7.45–7.43
(m, 2H), 7.39–7.20 (m, 10H), 6.36 (d, J¼8.3 Hz, 1H), 4.44–
4.38 (m, 2H), 4.28–4.25 (m, 1H), 3.86–3.82 (m, 1H),
+
0 29 3 3
found 360.2285.
2
1.95–1.86 (m, 2H), 1.70–1.44 (m, 3H), 1.28–1.18 (m,
.69–2.60 (m, 1H), 2.55–2.46 (m, 1H), 2.30–2.21 (m, 1H),
4
.2.1.9. (1S,2S,3aS,6aS)-2-(Benzylcarbamoyl)-1-((1-
oxidopyridin-2-yl)methyl)-octahydrocyclopenta[b]pyrrole
-oxide (1g). The title compound 1g was obtained by silica
1
3
1H) ppm; C NMR (100 MHz, CDCl ): d¼166.5, 150.6,
3
1
149.4, 141.7, 136.6, 129.5, 128.8, 128.6, 128.0, 127.6,
127.3, 127.1, 127.0, 124.1, 82.0, 78.4, 62.9, 71.9, 56.3,
41.8, 34.3, 32.6, 27.7, 25.4 ppm. HRMS (ESI) calcd for
gel column chromatography (ethyl acetate/methanol¼5:1,
ꢁ
120.1 (c 0.24, CHCl3). H NMR (400 MHz, CDCl3):
25
D
v/v) as a white solid in 87% yield. Mp 122–123 C. [a]
+
1
+
C H N O [M+H] : 428.2333, found 428.5461.
27 29 3 2
d¼11.58 (d, J¼5.2 Hz, 1H), 8.24 (d, J¼6.4 Hz, 1H), 7.60–
7
.58 (m, 1H), 7.33–7.21 (m, 7H), 5.05 (d, J¼12.0 Hz, 1H),
.62–4.55 (m, 2H), 4.41 (dd, J¼5.2, 5.2 Hz, 1H), 4.25 (d,
4.2.1.13. (1S,2S,3aS,6aS)-2-(Benzhydrylcarbamoyl)-
1-benzyl-octahydrocyclopenta[b]pyrrole 1-oxide (2b).
The title compound 2b was obtained by silica gel column
chromatography (ethyl acetate/petroleum ether¼2:1, v/v)
4
J¼11.6 Hz, 1H), 4.08 (dd, J¼5.6, 5.6 Hz, 1H), 2.75–2.66
(
(
(
1
1
2
3
m, 1H), 2.59–2.53 (m, 1H), 2.21–2.13 (m, 1H), 1.87–1.78
m, 2H), 1.67–1.64 (m, 1H), 1.50–1.44 (m, 2H), 1.22–1.19
ꢁ
25
D
as a white solid in 87% yield. Mp 55–58 C. [a] ꢀ15.1
1
3
1
m, 1H) ppm; C NMR (100 MHz, CDCl ): d¼167.3,
(c 0.25, CHCl ). H NMR (400 MHz, CDCl ): d¼12.01 (d,
3
3
3
41.6, 139.3, 138.6, 132.1, 128.7, 127.7, 127.3, 126.7,
J¼7.2 Hz, 1H), 7.45–7.20 (m, 15H), 6.33 (d, J¼6.8 Hz,
1H), 4.47–4.37 (m, 2H), 4.18–3.92 (m, 1H), 2.65–2.45 (m,
2H), 2.45–2.31 (m, 1H), 2.30–2.18 (m, 1H), 2.12–2.00
(m, 1H), 1.78–1.41 (m, 4H), 1.37–1.31 (m, 1H) ppm;
25.0, 83.7, 80.1, 63.1, 42.8, 42.2, 34.5, 32.8, 27.9,
4.7 ppm. HRMS (ESI) calcd for C H N O [M+Na] :
90.1788, found 390.4390.
+
2
1 25 3 3