Chemical Papers
m, CH2); 3.46–3.25 (m, 2H, CH2); 3.81–3.72 (m, 1H, CH);
5.11–5.01 (m, 2H, CH2); 5.83–5.82 (m, 1H, CH); 7.35–7.25
(m, 5H, ArH). 13C NMR (ppm): 24.9 (CH2); 27.7 (CH2);
29.3 (CH2); 29.8 (CH2); 32.8 (CH2); 33.1 (CH2); 33.4 (CH2);
34.5 (CH2); 44.0 (CH2); 48.6 (CH); 70.3 (C); 115.5 (CH2);
126.8 (ArCH); 128.8 (ArCH); 128.8 (ArCH); 137.0 (ArC);
138.5 (CH); 172.5 (C=O); 176.4 (C=O). HRMS (ESI+) m/z
calcd for C23H32N2O2 (M+H+) 369.2537, found 369.2536.
(ppm): 0.99 (s, 9H, 3CH3); 1.67 (s, 2H, CH2); 1.72 (s,
6H, 2CH3); 1.81–1.72 (m 2H, CH2); 2.22–2.02 (m, 4H,
CH2); 2.46–2.40 (m, 2H, CH2); 3.25–3.12 (m, 2H, CH2);
5.07–4.98 (m, 2H, CH2); 5.83–5.73 (m, 1H, CH); 6.86
(d, 1H, J = 4.2 Hz, C4H3S); 6.9 (dd, 1H, J = 5.4, 2.7 Hz,
C4H3S); 7.14 (d, 1H, J = 4.2 Hz, C4H3S). 13C NMR
(ppm): 27.7 (CH2); 28.9 (CH2); 29.0 (2CH3); 29.8 (CH2);
30.0 (CH2); 31.5 (3CH3); 31.7 (CH2); 33.8 (CH2); 44.0
(C); 52.4 (C); 55.8 (CH2), 70.5 (C); 115.5 (CH2); 123.9
(C3H2SCH); 125.4 (C3H2SCH); 127.1 (C3H2SCH); 137.0
(C3H2SC); 140.7 (CH); 172.0 (C=O); 176.3 (C=O).
HRMS (ESI+) m/z calcd for C23H36N2O2S (M + H+)
405.2573, found 405.2570.
rac‑2‑(But‑3‑en‑1‑yl)‑N‑cyclohexyl‑5‑oxo‑1‑(2‑(thiophen‑2
‑yl) ethyl) pyrrolidine‑2‑carboxamide (4b)
Yield (0.13 g, 75%), obtained as a pale oil (hexane: EtOAc
7:3, Rf =0.4); IR (cm−1): 3328 (N–H); 3078 (C-H, Ar); 2931
(C-H); 2853 (C-H); 1665 (C=O). 1H NMR (ppm): 1.75–1.18
(m, 10H, 5CH2); 1.91–1.83 (m, 2H, CH2); 2.23–2.12 (m,
4H, 2CH2); 2.51–2.45 (m, 2H, CH2); 3.25–3.19 (m, 2H,
CH2); 3.47- 3.38 (m, 2H, CH2); 3.81–3.70 (m, 1H, CH);
5.11–5.02 (m, 2H, CH2), 5.83–5.79 (m, 1H, CH); 6.89
(d, 1H, J = 6.5 Hz, C4H3S); 6.96 (dd, 1H, J = 5.2, 2.4 Hz,
C4H3S); 7.18 (d, 1H, J=6.4 Hz, C4H3S). 13C NMR (ppm):
25.4 (CH2); 27.7 (CH2); 28.5 (CH2); 29.3 (CH2); 29.8
(CH2); 32.5 (CH2); 33.0 (CH2), 33.6 (CH2); 44.0 (CH2);
48.7 (CH); 70.2 (C); 115.5 (CH2); 124.0 (C3H2SCH); 125.5
(C3H2SCH); 127.0 (C3H2SCH); 137.0 (C3H2SC); 140.7
(CH); 172.3 (C=O); 176.5 (C=O). HRMS (ESI+) m/z calcd
for C21H30N2O2S (M+H+) 375.2101, found 375.2098.
rac‑N‑Cyclohexyl‑5‑oxo‑2‑(pent‑4‑en‑1‑yl)‑1‑phenethyl‑
pyrrolidine‑2‑carboxamid e (4e)
Yield (0.132 g, 78%), obtained as a colorless oil (hexane:
EtOAc 7:3, Rf =0.5); IR (cm−1): 3325 (N–H); 3059 (C-H,
Ar); 2937 (C-H); 2856 (C-H); 1664 (C=O); 1524 (C=C).
1H NMR (ppm): 1.55–1.44 (m, 10H, 5CH2); 1.56–1.46 (m,
2H, CH2); 1.89–185 (m, 2H, CH2); 2.20–2.06 (m, 4H, CH2);
2.51–2.38 (m, 2H, CH2); 3.03–2.87 (m, 2H, CH2); 3.42–3.25
(m, 2H, CH2); 3.79–3.72 (m, 1H, CH); 5.07–4.98 (m, 2H,
CH2); 5.84–5.75 (m, 1H, CH); 7.34–7.22 (m, 5H, ArH).
13C NMR (ppm): 24.0 (CH2); 24.9 (CH2); 25.4 (CH2); 29.9
(CH2); 32.9 (CH2); 33.0 (CH2); 33.8 (CH2); 33.9 (CH2); 34.5
(CH2); 44.0 (CH2); 48.7 (CH); 70.2 (C); 115.5 (CH2); 126.7
(ArCH); 128.6 (ArCH); 128.8 (ArCH); 137.8 (ArC); 138.7
(CH); 172.7 (C=O); 176.5 (C=O). HRMS (ESI+) m/z calcd
for C24H34N2O2 (M+H+) 383.2693, found 383.2693.
rac‑2‑(But‑3‑en‑1‑yl)‑5‑oxo‑1‑phenethyl‑N‑(2,4,4‑trimethyl‑
pentan‑2‑yl) pyrrolidine‑2‑carboxamide (4c)
Yield (0.135 g, 75%), obtained as a colorless oil (hexane:
EtOAc 7:3, Rf =0.4); IR (cm−1): 3335 (N–H); 3070 (C-H,
Ar); 2951 (C-H); 2870 (C-H); 1671 (C=O); 1524 (C=C).
1H NMR (ppm): 0.99 (s, 9H, 3CH3); 1.66 (s, 2H, CH2);
1.73 (s, 6H, 2CH3); 1.99–1.90 (m, 4H, 2CH2), 2.23–2.06
(m, 4H, CH2); 2.47–2.42 (m, 2H, CH2); 3.04–2.88 (m, 2H,
CH2); 5.08–4.98 (m, 2H, CH2); 5.84–5.74 (m, 1H, CH);
7.30–7.23 (m, 5H, ArH). 13C NMR (ppm): 27.7 (CH2); 28.2
(CH2); 28.8 (CH2); 29.0 (2CH3); 31.6 (CH2); 31.7 (3CH3);
33.7 (CH2); 34.6 (CH2); 44.5 (C); 52.5 (C); 55.8 (CH2);
70.5 (C); 115.4 (CH2); 126.7 (ArCH); 128.5 (ArCH); 128.8
(ArCH); 137.0 (ArC); 138.7 (CH); 172.0 (C=O); 176.2
(C=O). HRMS (ESI+) m/z calcd for C25H38N2O2 (M+H+)
399.3006, found 399.3005.
rac‑N‑Cyclohexyl‑5‑oxo‑2‑(pent‑4‑en‑1‑yl)‑1‑(2‑(thiophen‑2
‑yl) ethyl) pyrrolidine‑2‑carboxamide (4f)
Yield (0.130 g, 75%), obtained as a brown oil (hexane:
EtOAc 7:3, Rf =0.5); IR (cm−1): 3318 (N–H); 3077 (C-H,
1
Ar); 2926 (C-H); 2856 (C-H); 1674 (C=O). H NMR
(ppm): 1.52–1.42 (m, 10H, 5CH2); 1.55–1.46 (m, 2H,
CH2); 1.88–184 (m, 2H, CH2); 2.21–2.05 (m, 4H, m, CH2);
2.51–2.40 (m, 2H, CH2); 3.28–3.11 (m, 2H, CH2); 3.48–3.32
(m, 2H, CH2); 3.79–3.71 (m, 1H, CH); 5.07–5.00 (m, 2H,
CH2); 5.84–5.74 (m, 1H, CH); 6.88 (d, 1H, J = 5.1 Hz,
C4H3S); 6.96 (dd, 1H, J = 4.8, 2.3 Hz, C4H3S); 7.18 (d,
1H, J=5.1 Hz, C4H3S). 13C NMR (ppm): 22.8 (CH2); 24.9
(CH2); 25.4 (CH2); 28.5 (CH2); 29.5 (CH2); 29.9 (CH2);
32.9 (CH2); 33.7 (CH2); 33.9 (CH2); 44.1 (CH2); 48.7
(CH); 70.4 (C); 115.7 (CH2); 124.0 (C3H2SCH); 125.5
(C3H2SCH); 127.0 (C3H2SCH); 136.7 (C3H2SC); 140.7
(CH); 172.5 (C=O); 176.5 (C=O). HRMS (ESI+) m/z calcd
for C22H32N2O2S (M+H+) 389.2258, found 389.2257.
rac‑2‑(But‑3‑en‑1‑yl)‑5‑oxo‑1‑(2‑(thiophen‑2‑yl)
ethyl)‑N‑(2,4,4‑trimethyl pentan‑2‑yl) pyrrolidine‑2‑carbox‑
amide (4d)
Yield (0.13 g, 70%), obtained as a pale oil (hexane:
EtOAc 7:3, Rf = 0.3); IR (cm−1): 3342 (N–H); 3077 (C-H,
1
Ar); 2954 (C-H); 2867 (C-H); 1667 (C=O). H NMR
1 3