The Journal of Organic Chemistry
Page 16 of 23
1
2
3
4
5
6
7
8
9
1
1
1
1
1
1
1
1
1
1
2
2
2
2
2
2
2
2
2
2
3
3
3
3
3
3
3
3
3
3
4
4
4
4
4
4
4
4
4
4
5
5
5
5
5
5
5
5
5
5
6
1
19.7, 119.4, 108.4, 108.1, 66.4, 65.6, 52.0, 51.8, 45.0, 44.9, 21.4, 16.1, 15.6, 15.5. HRMS [ESI]: m/z calculated for
+
C
17
H
21NO
2
[M] 271.1567, found 271.1570. IR (ATR): ν= 3951 (w), 1753 (vs), 1458 (m), 1265(m), 1165 (m), 718 (vs),
-1
698 (s) cm .
methyl 2-methyl-5-phenyl-3-(1H-pyrrol-1-yl)pentanoate (9ua). Yield: colorless oil, 22 mg, 0.08 mmol. Mixture of
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
3
diastereomers. H NMR (400 MHz, CDCl ) δ 7.38 – 7.26 (m, 2H), 7.27 – 7.18 (m, 2H), 7.17 – 7.06 (m, 2H), 6.70 (m,
2H), 6.23 (t, 2H (minor)), 6.19 (t, 2H (major)), 4.1 (m, 1H (major)) , 4.05 (m, 1H (minor)), 3.72 (s, 1H (minor)), 3.54 (3H
(
major)), 2.88 (1H), 2.52 – 2.34 (2H), 2.30 – 1.98 (2H), 1.23 (3H (major)), 0.94 (3H (minor)). 13C{1H} NMR (101 MHz,
CDCl
3
) δ 175.0, 174.5, 141.02, 140.97, 128.5, 128.4, 126.1, 126.0, 119.5, 119.4, 108.3, 108.0, 61.5, 61.4, 51.9, 51.8,
+
46.7, 46.5, 35.9, 33.8, 32.2, 32.0, 14.6, 14.4. HRMS [EI]: m/z calculated for C17
H
21NO
2
[M] 271.1567, found 271.1568.
-1
IR (ATR): ν= 2951 (w), 1732 (s), 1265 (m), 1161 (m), 721 (vs), 698 (vs) cm .
methyl 3-cyclohexyl-2-methyl-3-(1H-pyrrol-1-yl)propanoate (9ta). Yield: colorless oil, 59 mg, 0.237 mmol. Mixture
1
of diastereomers. H NMR (400 MHz, CDCl
3
) δ 6.61 (m, 2H), 6.12 (m, 2H), 3.99 (dd, J = 8.6, 7.0 Hz, 1H (minor)), 3.89
(dd, J = 8.2, 6.6 Hz, 01H (major)), 3.71 (s, 3H (minor)), 3.57 (s, 3H (major)), 3.22 – 2.95 (m, 1H), 1.89 (dddd, J = 11.7,
8
2
6
.7, 6.5, 3.3 Hz, 1H), 1.82 – 1.44 (m, 6H), 1.22 (d, J = 7.0 Hz, 3H), 1.18 – 1.07 (m, 2H (major)), 1.01 (d, J = 7.0 Hz,
H(minor)), 0.96 – 0.77 (m, 1H). 13C{1H} NMR (101 MHz, CDCl
) δ 175.3, 174.7, 120.8, 120.6, 107.5, 107.1, 67.4,
3
6.8, 51.9, 51.7, 42.5, 42.0, 41.2, 39.4, 30.9, 30.6, 28.7, 28.0, 26.3, 26.24, 26.21, 26.17, 26.12, 15.0, 13.49.HRMS [EI]:
+
m/z calculated for C15
H
23NO
2
[M] 249.1729, found 249.1724. IR (ATR): ν= 2973 (m), 2855 (m), 1735 (s), 1261 (m),
-1
1165 (m), 721 (vs) cm .
methyl 3-(4-methoxyphenyl)-2-methyl-3-(1H-pyrrol-1-yl)propanoate (9fa). Yield: colorless oil, 20.2 mg,
1
0.074 mmol. Mixture of diastereomers. H NMR (400 MHz, CDCl
3
) δ 7.37 – 7.23 (m, 2H), 6.99 – 6.82 (m, 2H), 6.76 (m,
2H), 6.16 (m, 2H (minor)), 6.11 (m, 2H (major)), 5.16 (m, 1H), 3.80 (m, 3H), 3.60 (s, 3H (major)), 3.56 (s, 3H (minor)),
3
.43 (m, 1H), 1.14 (m, 3H). 13C{1H} NMR (101 MHz, CDCl
3
) δ 174.9, 174.5, 159.4, 159.2, 131.7, 130.8, 129.9, 128.6,
128.2, 119.5, 119.3, 114.2, 114.0, 113.8, 108.5, 108.2, 65.7, 65.1, 55.3, 55.2, 52.1, 51.9, 45.3, 45.1, 29.7, 16.0, 15.6.
+
HRMS [EI]: m/z calculated for C16H19NO
3
[M] 273.1359, found 273.1355. IR (ATR): ν= 2951 (w), 1735 (s), 1512 (s),
-1
1250 (m), 1165 (s), 723 (vs), 629 (s) cm .
methyl (syn)-2-methyl-3-(naphthalen-2-yl)-3-(1H-pyrrol-1-yl)propanoate (syn 9sa). Yield: colorless solid,
1
47.4 mg, 0.162 mmol, 41%. H NMR (400 MHz, CDCl
3
) δ 7.86 – 7.79 (m, 3H), 7.58 – 7.42 (m, 3H), 6.84 (t, J = 2.2 Hz,
13
2H), 6.20 (t, J = 2.1 Hz, 2H), 5.39 (d, J = 11.0 Hz, 1H), 3.67 – 3.59 (m, 1H), 3.55 (s, 3H), 1.23 (d, J = 6.9 Hz, 3H). C{1H}
NMR (101 MHz, CDCl
3
) δ 174.5, 136.8, 133.2, 133.0, 128.7, 128.2, 127.6, 126.3, 126.3, 125.6, 125.3, 119.8, 108.7,
+
65.6, 52.0, 44.9, 15.7. HRMS [EI]: m/z calculated for C19
H
19NO
2
[M] 293.1410, found 293.1414. IR (ATR): ν= 2935
w), 1720 (vs), 1357 (m), 1269 (m), 1177 (m), 725 (vs), 383 (vs) cm-1.
(
ACS Paragon Plus Environment