Page 13 of 17
The Journal of Organic Chemistry
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NMR (600 MHz, CDCl
3
) δ 4.31 – 4.27 (m, 2H), 3.67 – 3.63 (m, 2H), 2.55 (dd, J = 5.0, 4.0 Hz, 1H), 1.94 –
1.85 (m, 1H), 1.80 – 1.66 (m, 5H), 1.53 – 1.46 (m, 1H), 1.29 – 1.12 (m, 6H), 1.03 (d, J = 7.0 Hz, 1H), 0.98 (d,
1
3
1
3
J = 7.0 Hz, 1H); C NMR{ H} (150 MHz, CDCl ) δ 159.0, 69.0, 61.2, 48.2, 39.4, 30.9, 29.4, 28.8, 27.0, 26.9,
+
263.1735, found 263.1732; IR (film) (cm-1)
2
3
6.7, 20.5, 18.8; HRMS (ESI) [M+Na] calcd for C13H N NaO
24 2 2
295, 2976, 2963, 2913, 1758, 1743, 1602, 1508, 1479, 1410, 1260, 1221, 1103, 1031.
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-[(1-(4-Trifluoromethylphenyl)-1-cyclohexanyl)methyl]amino-2-oxazolidinone (2db). White solid (75
1
mg, 69%); H NMR (600 MHz, CDCl
3
) δ 7.59 (d, J = 8.0 Hz, 2H), 7.46 (d, J = 8.0 Hz, 2H), 4.15 (ddd, J = 8.5,
8.5, 5.0 Hz, 1H), 4.04 (d, J = 7.0 Hz, 1H), 4.00 (ddd, J = 8.5, 8.5, 8.5 Hz, 1H), 3.45 (ddd, J = 8.5, 8.5, 8.5 Hz,
H), 3.05 (ddd, J = 8.5, 8.5, 5.0 Hz, 1H), 1.92 (bd, J = 12.5 Hz, 1H), 1.81 – 1.74 (m, 1H), 1.67 – 1.59 (m, 3H),
1
1
3
1
1.44 – 1.38 (m, 1H), 1.28 – 1.21 (m, 1H), 1.16 – 1.04 (m, 3H), 0.87 – 0.78 (m, 1H); C NMR{ H} (150 MHz,
CDCl
) δ 159.1, 145.2, 129.8 (q, 2JCF = 32 Hz), 125.1 (q, 3JCF = 3.5 Hz), 124.3 (q, 1JCF = 270 Hz), 69.3, 61.5,
3
+
4
3
8.1, 42.1, 30.1, 29.0, 26.3, 26.1, 26.1; HRMS (ESI) [M+Na] calcd for C17
H
21
F
3
N
2
NaO
2
365.1453, found
-
1
65.1448; IR (film) (cm ) 3319, 2919, 2852, 1756, 1618, 1478, 1409, 1324, 1259, 1157, 1130, 1067, 1019.
3
-[1-(1-(4-Trifluoromethylphenyl)-2,2-dimethyl)propyl]amino-2-oxazolidinone (2dc). White solid (89
1
mg, 80%); H NMR (600 MHz, CDCl
3
) δ 7.58 (d, J = 8.0 Hz, 2H), 7.52 (bs, 2H), 4.68 (s, 1H), 4.13 (ddd, J =
9.0, 9.0, 4.0 Hz, 1H), 4.05 (s, 1H), 3.96 (ddd, J = 9.0, 9.0, 9.0 Hz, 1H), 3.48 (ddd, J = 9.0, 9.0, 9.0 Hz, 1H),
1
3
1
3
.12 (ddd, J = 9.0, 9.0, 4.0 Hz, 1H), 0.97 (s, 9H); C NMR{ H} (150 MHz, CDCl
3
) δ 159.2, 144.3, 129.9 (bs),
129.7 (q, 2JCF = 32 Hz), 124.5 (q, 3JCF = 3.5 Hz), 124.3 (q, 1JCF = 270 Hz), 72.9, 61.5, 47.9, 34.2, 26.9; HRMS
+
-1
(
ESI) [M+Na] calcd for C15
H
19
F
3
N
2
NaO
2
339.1296, found 339.1293; IR (film) (cm ) 3311, 2975, 2906, 2873,
1
749, 1619, 1481, 1402, 1324, 1256, 1164, 1110, 1076, 1017.
1
3
-[1-(1-(4-Trifluoromethylphenyl))pentyl]amino-2-oxazolidinone (2dd). Colorless oil (56 mg, 49%); H
NMR (600 MHz, CDCl
3
) δ 7.60 (d, J = 8.0 Hz, 2H), 7.50 (d, J = 8.0 Hz, 2H), 4.23 (dd, J = 9.0, 5.5 Hz, 1H),
4
.18 (ddd, J = 8.5, 8.5, 5.0 Hz, 1H), 4.04 (ddd, J = 8.5, 8.5, 8.5 Hz, 1H), 3.47 (ddd, J = 8.5, 8.5, 8.5 Hz, 1H),
3.10 (ddd, J = 8.5, 8.5, 5.0 Hz, 1H), 1.79 – 1.72 (m, 1H), 1.65 – 1.57 (m, 1H), 1.33 – 1.23 (m, 3H), 1.14 – 1.05
m, 1H), 0.84 (t, J = 7.0 Hz, 3H); 13C NMR{ H} (150 MHz, CDCl
1
) δ 159.1, 146.3, 130.0 (q, 2JCF = 32 Hz),
(
3
128.4, 125.5 (q, 3JCF = 3.5 Hz), 124.3 (q, 1JCF = 270 Hz), 64.3, 61.5, 48.2, 35.1, 28.0, 22.8, 14.0; HRMS (ESI)
+
-1
[
M+Na] calcd for C15
H
19
F
3
N
2
NaO
2
339.1296, found 339.1293; IR (film) (cm ) 3278, 2960, 2933, 2874, 1762,
1
619, 1480, 1404, 1326, 1251, 1165, 1125, 1068, 1033.
1
3
-[1-(1-(4-Trifluoromethylphenyl))propyl]amino-2-oxazolidinone (3d). Colorless oil (96 mg, 82%); H
NMR (600 MHz, CDCl
3
) δ 7.61 (d, J = 8.0 Hz, 2H), 7.50 (d, J = 8.0 Hz, 2H), 4.46 (bs, 1H), 4.21 – 4.15 (m,
2
1
1
H), 4.06 (ddd, J = 8.5, 8.5, 8.5 Hz, 1H), 3.49 (ddd, J = 8.5, 8.5, 8.5 Hz, 1H), 3.14 (ddd, J = 8.5, 8.5, 5.0 Hz,
H), 1.85 – 1.77 (m, 1H), 1.69 – 1.60 (m, 1H), 0.82 (t, J = 7.5 Hz, 3H); 13C NMR{ H} (150 MHz, CDCl
1
) δ
3
59.1, 145.9, 130.0 (q, 2JCF = 32 Hz), 128.5, 125.4 (q, 3JCF = 3.5 Hz), 125.8 (q, 1JCF = 270 Hz), 65.6, 61.5, 48.2,
+
-1
28.2, 10.2; HRMS (ESI) [M+Na] calcd for C13
15 3 2 2
H F N NaO 311.0983, found 311.0979; IR (film) (cm ) 3267,
2
969, 2939, 2884, 1771, 1746, 1538, 1414, 1324, 1262, 1160, 1103, 1067, 1043.
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