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The Journal of Organic Chemistry
107-110 °C; 1H NMR (500 MHz, CDCl3) δ 8.01 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 8.3 Hz, 1H), 7.67 (t, J = 7.6 Hz, 1H),
7.53 (t, J = 7.6 Hz, 1H), 7.32 (s, 1H), 6.08 (d, J = 8.6 Hz, 1H), 5.41 – 5.14 (m, 1H), 4.70 (dq, J = 9.0, 4.8, 4.3 Hz, 1H),
3.12 (dd, J = 15.5, 5.3 Hz, 1H), 2.95 (dd, J = 15.5, 6.6 Hz, 1H), 2.68 (s, 3H), 1.80 – 1.68 (m, 2H), 1.63 (d, J = 7.6 Hz,
2H), 1.47 (s, 9H), 1.38 – 1.09 (m, 6H). 13C{1H} NMR (126 MHz, CDCl3) δ 170.9 , 159.3 , 155.4 , 147.2 , 144.8 , 129.7
, 129.1 , 127.4 , 126.1 , 123.6 , 120.7 , 79.5 , 72.8 , 52.3 , 40.0 , 31.5 , 28.4 , 25.3 , 23.6 , 18.8 . HRMS(ESI) m/z: [M +
H]+ Caled for C24H33N2O4 413.2435; found 413.2442.
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tert-butyl (2-phenyl-1-(quinolin-2-yl)ethyl)carbamate (13) Following the general procedure condition A, 13 was
purified by silica gel chromatography (PE:EA=5:1) ; 38.3 mg (55%); white solid; mp : 129-132 °C; H NMR (500
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MHz, CDCl3) δ 8.06 (d, J = 8.5 Hz, 1H), 7.96 (d, J = 8.4 Hz, 1H), 7.77 (d, J = 8.1 Hz, 1H), 7.71 (t, J = 7.7 Hz, 1H),
7.52 (t, J = 7.4 Hz, 1H), δ 7.2 – 7.1 (m, 3H), 7.0 – 7.0 (m, 2H), 7.0 (d, J = 8.4 Hz, 1H).5.16 (q, J = 7.1 Hz, 1H), 3.34
(dd, J = 13.5, 5.6 Hz, 1H), 3.15 (dd, J = 13.1, 8.0 Hz, 1H), 1.46 (s, 9H). 13C{1H} NMR (126 MHz, CDCl3) δ 159.7 ,
155.3 , 147.5 , 137.4 , 135.9 , 129.6 , 129.4 , 129.1 , 128.1 , 127.5 , 127.3 , 126.3 , 126.2 , 120.6 , 79.3 , 57.1 , 42.8 ,
28.4 . HRMS(ESI) m/z: [M + H]+ Caled for C22H25N2O2 349.1911; found 349.1917.
tert-butyl (2-phenyl-1-(4-phenylquinolin-2-yl)ethyl)carbamate (14) Following the general procedure condition A,
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14 was purified by silica gel chromatography (PE:EA=5:1) ; 63.6 mg (75%); white solid; mp : 147-150 °C; H NMR
(500 MHz, CDCl3) δ 8.15 (d, J = 8.4 Hz, 1H), 7.87 (d, J = 8.3 Hz, 1H), 7.72 (t, J = 7.7 Hz, 1H), 7.47 (dt, J = 7.6, 4.8
Hz, 4H), 7.32 (d, J = 6.7 Hz, 2H), 7.20 (d, J = 5.8 Hz, 3H), 7.04 (d, J = 6.6 Hz, 2H), 6.83 (s, 1H), 6.25 (d, J = 7.7 Hz,
1H), 5.19 (q, J = 7.3 Hz, 1H), 3.40 (dd, J = 13.3, 5.7 Hz, 1H), 3.14 (dd, J = 13.2, 7.9 Hz, 1H), 1.48 (s, 9H). 13C{1H}
NMR (126 MHz, CDCl3) δ 159.1 , 155.3 , 148.1 , 148.0 , 137.9 , 137.5 , 129.7 , 129.5 , 129.4 , 129.2 , 128.4 , 128.3 ,
128.2 , 126.3 , 126.2 , 125.8 , 125.7 , 120.8 , 79.3 , 57.2 , 43.1 , 28.4 . HRMS(ESI) m/z: [M + H]+ Caled for
C28H29N2O2 425.2224; found 425.2230.
tert-butyl (1-(3-methylquinolin-2-yl)-2-phenylethyl)carbamate (15) Following the general procedure condition A,
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15 was purified by silica gel chromatography (PE:EA=5:1) ; 55.8 mg (77%); white solid; mp : 129-132 °C; H NMR
(500 MHz, CDCl3) δ 8.06 (d, J = 8.4 Hz, 1H), 7.78 (s, 1H), 7.73 (d, J = 8.1 Hz, 1H), 7.67 (t, J = 7.6 Hz, 1H), 7.51 (t, J
= 7.5 Hz, 1H), 7.20 – 7.15 (m, 3H), 7.00 (dt, J = 7.3, 3.6 Hz, 2H), 6.22 (d, J = 8.5 Hz, 1H), 5.40 (q, J = 7.7 Hz, 1H),
3.30 – 3.16 (m, 2H), 2.19 (s, 3H), 1.48 (s, 9H). 13C{1H} NMR (126 MHz, CDCl3) δ 159.7 , 155.2 , 146.2 , 137.4 ,
136.0 , 129.6 , 128.9 , 128.7 , 128.4 , 128.0 , 127.4 , 126.7 , 126.2 , 126.2 , 79.1 , 53.1 , 43.0 , 28.4 , 18.3 . HRMS(ESI)
m/z: [M + H]+ Caled for C23H27N2O2 363.2067; found 363.2074.
tert-butyl (1-(6-chloroquinolin-2-yl)-2-phenylethyl)carbamate (16) Following the general procedure condition A,
16 was purified by silica gel chromatography (PE:EA=10:1) ; 39.0 mg (51%); white solid; mp : 118-121 °C; 1H NMR
(500 MHz, CDCl3) δ 7.99 (d, J = 8.9 Hz, 1H), 7.87 (d, J = 8.4 Hz, 1H), 7.75 (d, J = 2.3 Hz, 1H), 7.63 (dd, J = 9.0, 2.4
Hz, 1H), 7.20 – 7.10 (m, 3H), 6.97 (q, J = 3.8 Hz, 3H), 6.07 (d, J = 7.7 Hz, 1H), 5.14 (q, J = 7.3 Hz, 1H), 3.31 (dd, J =
13.3, 5.6 Hz, 1H), 3.13 (dd, J = 13.2, 8.0 Hz, 1H), 1.45 (s, 9H). 13C{1H} NMR (126 MHz, CDCl3) δ 160.2 , 155.3 ,
145.9 , 137.2 , 135.0 , 131.9 , 130.7 , 130.4 , 129.6 , 128.2 , 127.8 , 126.4 , 126.2 , 121.4 , 79.4 , 57.1 , 42.7 , 28.4 .
HRMS(ESI) m/z: [M + H]+ Caled for C22H24ClN2O2 383.1521; found 383.1527.
tert-butyl (1-(4-chloroquinolin-2-yl)ethyl)carbamate (17) Following the general procedure condition A, 17 was
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purified by silica gel chromatography (PE:EA=10:1) ; 36.1 mg (59%); white solid; mp : 130-135 °C; H NMR (400
MHz, CDCl3) δ 8.19 (d, J = 8.4 Hz, 1H), 8.07 (d, J = 8.4 Hz, 1H), 7.75 (t, J = 8.3 Hz, 1H), 7.60 (t, J = 7.6 Hz, 1H), 7.45
(s, 1H), 6.02 (d, J = 6.7 Hz, 1H), 5.03 – 4.91 (m, 1H), 1.54 (d, J = 6.8 Hz, 3H), 1.47 (s, 9H). 13C{1H} NMR (101 MHz,
CDCl3) δ 161.8 , 155.2 , 148.2 , 143.0 , 130.4 , 129.4 , 127.2 , 125.4 , 124.0 , 119.4 , 79.4 , 51.4 , 28.4 , 22.5 .
HRMS(ESI) m/z: [M + H]+ Caled for C16H20ClN2O2 307.1208; found 307.1217.
tert-butyl (1-(4-phenylquinolin-2-yl)ethyl)carbamate (18) Following the general procedure condition A, 18 was
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purified by silica gel chromatography (PE:EA=10:1) ; 50.1 mg (72%); white solid; mp : 160-163 °C; H NMR (500
MHz, CDCl3) δ 8.14 (d, J = 8.4 Hz, 1H), 7.88 (d, J = 9.3 Hz, 1H), 7.71 (t, J = 8.3 Hz, 1H), 7.58 – 7.39 (m, 6H), 7.28 (s,
1H), 7.26 (s, 1H), 6.25 (d, J = 7.1 Hz, 1H), 5.19 – 4.86 (m, 1H), 1.58 (d, J = 6.8 Hz, 3H), 1.49 (s, 9H). 13C{1H} NMR
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