10.1002/adsc.202100305
Advanced Synthesis & Catalysis
1435.91, 1306.80, 1142.21, 1011.14, 902.34, 754.62,
662.47, 578.17.
3428.05, 2933.54, 1722.08, 1595.62, 1438.66, 1154.72,
1005.44, 786.41, 699.97, 643.27, 546.48.
Methyl 2-(3-fluorophenyl)-2-(3,5-dimethyl-1H-pyrrol-2-
yl)acetate, (3l): Following the general procedure the
desired compound 3l was prepared in 111.2 mg, 81% yield
as deep red oil. The eluent was EtOAc/n-hexane (15:85).
Ethyl 2-(3,5-dimethyl-1H-pyrrol-2-yl)-2-(p-tolyl)acetate,
(3p): Following the general procedure the desired
compound 3p was prepared in 115.5 mg, 81% yield as
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deep red oil. The eluent was EtOAc/n-hexane (15:85). H
1H NMR (CDCl3, 400 MHz) δH 8.49 (s, 1H), 7.32-7.28 (m, NMR (CDCl3, 400 MHz) δH 8.49 (s, 1H), 7.15-7.10 (m,
1H), 7.05-7.03 (m, 1H), 6.98-6.94 (m, 2H), 5.73 (d, J = 2
Hz, 1H), 5.07 (s, 1H), 3.79 (s, 3H), 2.26 (s, 3H), 1.99 (s,
3H); 13C NMR (CDCl3, 100 MHz) δC 173.13, 164.33,
161.88, 141.27, 141.20, 130.32, 130.24, 127.21, 123.31,
123.28, 116.68, 114.86, 114.64, 114.46, 114.25, 108.19,
52.66, 47.38, 47.37, 13.17, 10.82; HRMS (ESI-TOF) m/z
4H), 5.70-5.69 (d, J = 4 Hz, 1H), 5.00 (s, 1H), 4.23-4.18 (q,
J = 8 Hz, 2H), 2.32 (s, 3H), 2.23 (s, 3H), 1.97 (s, 3H),
1.30-1.27 (t, J = 8 Hz, 3H); 13C NMR (CDCl3, 100 MHz)
δC 173.31, 136.95, 135.97, 129.53, 127.46, 126.65, 121.67,
116.08, 107.98, 61.42, 47.49, 21.14, 14.27, 13.17, 10.85;
HRMS (ESI-TOF) m/z calcd for C17H21NO2 [M + H]+
calcd for C15H16FNO2 [M + H]+ 262.1238, found 262.1248. 272.1645, found 272.1639. FT-IR (Neat) max (cm-1) =
FT-IR (Neat) max (cm-1) = 3395.07, 2926.76, 1722.16,
1589.86, 1438.40, 1238.58, 1154.34, 1009.24, 943.77,
877.06, 778.55, 686.71, 522.45.
3364.85, 2923.55, 1717.14, 1512.30, 1447.14, 1373.89,
1155.40, 1024.82, 784.12, 640.36, 499.92.
Dimethyl 2-(3,5-dimethyl-1H-pyrrol-2-yl)malonate, (3q):
Following the general procedure the desired compound 3q
was prepared in 91.2 mg, 77% yield as brown oil. The
eluent was EtOAc/n-hexane (25:75). 1H NMR (CDCl3, 400
MHz) δH 8.49 (s, 1H), 5.69-5.68 (d, J = 4 Hz, 1H), 4.74 (s,
1H), 3.76 (s, 6H), 2.22 (s, 3H), 2.02 (s, 3H); 13C NMR
(CDCl3, 100 MHz) δC 168.56, 128.09, 117.97, 115.78,
108.07, 53.06, 48.57, 13.15, 10.81; HRMS (ESI-TOF) m/z
calcd for C11H15NO4 [M + H]+ 226.1074, found 226.1068.
FT-IR (Neat) max (cm-1) = 3394.47, 2922.11, 1720.62,
1435.03, 1314.67, 1263.11, 1139.44, 102.10, 791.66,
644.12, 564.05.
Methyl
2-(3,5-dimethyl-1H-pyrrol-2-yl)-2-(3-
methoxyphenyl)acetate, (3m): Following the general
procedure the desired compound 3m was prepared in 117.7
mg, 82% yield as deep red oil. The eluent was EtOAc/n-
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hexane (15:85). H NMR (CDCl3, 400 MHz) δH 8.45 (s,
1H), 7.25-7.21 (m, 1H), 6.85-6.78 (m, 3H), 5.70-5.69 (d, J
= 4 Hz, 1H), 5.03 (s, 1H), 3.78 (s, 3H), 3.76 (s, 3H), 2.23
(s, 3H), 1.99 (s, 3H); 13C NMR (CDCl3, 100 MHz) δC
173.40, 159.96, 140.23, 129.86, 126.86, 121.13, 119.97,
116.34, 113.81, 112.36, 108.08, 55.31, 52.52, 47.71, 13.16,
10.86; HRMS (ESI-TOF) m/z calcd for C16H19NO3 [M +
H]+ 274.1438, found 274.1426. FT-IR (Neat) max (cm-1) =
3401.79, 2924.71, 1724.87, 1592.55, 1439.57, 1252.89,
1150.25, 1035.42, 870.28, 780.07, 691.90, 553.28, 447.20.
Methyl 2-benzyl-6-phenyl-2-azabicyclo[3.1.0]hex-3-ene-6-
carboxylate, (4a): Following the general procedure, the
desired compound 4a was prepared in 68.95 mg, 71% yield
(dr: 2.2:1) as yellow oil. The eluent was EtOAc/n-hexane
Methyl 2-(3-bromophenyl)-2-(3,5-dimethyl-1H-pyrrol-2-
yl)acetate, (3n): Following the general procedure the
desired compound 3n was prepared in 135.8 mg, 80%
yield as deep red oil. The eluent was EtOAc/n-hexane
(15:85). 1H NMR (CDCl3, 400 MHz) δH 8.46 (s, 1H), 7.39-
7.36 (m, 2H), 7.17-7.15 (m, 2H), 5.70 (d, J = 2 Hz, 1H),
5.01 (s, 1H), 3.76 (s, 3H), 2.24 (s, 3H), 1.96 (s, 3H); 13C
NMR (CDCl3, 100 MHz) δC 173.03, 140.99, 130.65,
130.57, 130.39, 127.26, 126.34, 122.93, 120.43, 116.70,
108.23, 52.71, 47.33, 13.16, 10.85; HRMS (ESI-TOF) m/z
calcd for C15H16BrNO2 [M + H]+ 322.0437, found
322.0451. FT-IR (Neat) max (cm-1) = 3421.65, 2949.66,
1722.54, 1572.34, 1428.88, 1320.68, 1254.76, 1156.45,
1081.44, 1007.80, 879.32, 784.40, 655.80, 545.32.
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(15:85). H NMR (CDCl3, 400 MHz) δH 8.03-8.01 (d, J =
4.0 Hz, 2H), 7.54-7.50 (t, J = 8 Hz, 4H), 7.30-7.28 (t, J = 8
Hz, 2H), 7.21-7.19 (m, 1H), 6.93-6.91 (d, J = 8 Hz, 1H),
6.66-6.65 (m, 1H), 6.18-6.16 (m, 1H), 4.92-4.84 (m, 2H),
3.98 (s, 3H), 3.63 (s, 2H); 13C NMR (CDCl3, 100 MHz)
δC 186.18, 172.02, 164.18, 137.85, 137.39, 135.13,
132.58, 130.24, 129.05, 128.85, 128.72, 128.67, 128.55,
128.50, 127.64, 127.62, 126.58, 122.80, 120.12, 109.43,
107.56, 52.92, 52.51, 50.73, 49.77, 29.84; HRMS (ESI-
TOF) m/z calcd for C20H19NO2 [M + H]+ 306.1489, found
306.1500. FT-IR (Neat) max (cm-1) = 2929.46, 1733.23,
1689.77, 1594.10, 1443.72, 1301.61, 1199.09, 1000.74,
693.61.
Methyl 2-(3,5-dimethyl-1H-pyrrol-2-yl)-2-phenylacetate,
(3o): Following the general procedure the desired
compound 3o was prepared in 89.50 mg,70% yield as deep
Methyl
2-benzyl-6-(3-fluorophenyl)-2-
azabicyclo[3.1.0]hex-3-ene-6-carboxylate, (4b): Following
the general procedure, the desired compound was prepared
in 78.16 mg, 76% (dr:1.7:1) yield as yellow oil. The eluent
was EtOAc/n-hexane (15:85). 1H NMR (CDCl3, 400 MHz)
δH 6.94-6.68 (m, 8H), 6.16-6.15 (d, J = 4 Hz, 3H), 4.92 (s,
1H), 4.87 (s, 1H), 4.82-4.81 (d, J = 8 Hz, 2H), 3.63 (s, 3H);
13C NMR (CDCl3, 100 MHz) δC 171.50, 164.19, 161.74,
139.82, 139.75, 137.67, 128.86, 127.71, 126.46, 124.30,
124.28, 123.09, 115.90, 115.68, 114.70, 114.49, 100.57,
107.67, 52.64, 50.79, 49.32, 49.31, 29.83; HRMS (ESI-
TOF) m/z calcd for C20H18FNO2 [M + H]+ 324.1394, found
1
red oil. The eluent was EtOAc/n-hexane (15:85). H NMR
(CDCl3, 400 MHz) δH 8.49 (s, 1H), 7.36-7.32 (m, 2H),
7.29-7.26 (m, 3H), 5.74-5.73 (d, J = 4 Hz, 1H), 5.10 (s,
1H), 3.79 (s, 3H), 2.26 (s, 3H), 2.01 (s, 3H); 13C NMR
(CDCl3, 100 MHz) δC 173.57, 138.75, 128.87, 127.61,
127.36, 126.86, 121.29, 116.34, 108.06, 52.51, 47.75,13.17,
10.85; HRMS (ESI-TOF) m/z calcd for C15H17NO2 [M +
H]+ 244.1332, found 244.1321; FT-IR (Neat) max (cm-1) =
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