HETEROCYCLES, Vol. 82, No. 1, 2010
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H, 6.85; N, 7.32. Found: C, 70.08; H, 7.12, N, 7.19.
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(S)-4-Benzyl-3-methylmorpholin-2-one (2c). [α]D +16.5 (c 0.98, CHCl3); IR (neat) 3024, 1735 cm−1;
1H NMR (200 MHz, CDCl3) δ 7.30 (m, 5 H), 4.27 (m, 2H), 3.95 (d, J = 13.2 Hz, 1H), 3.36 (q, J = 6.8 Hz,
1H), 3.30 (d, J = 13.2 Hz, 1H), 2.85 (dt, J = 12.7, 3.6 Hz, 1H), 2.48 (dt, J = 12.7, 3.6 Hz, 1H), 1.54 (d, J =
6.8 Hz, 3H); 13C NMR (50 MHz, CDCl3) δ 170.7, 137.2, 129.4, 128.7, 127.0, 68.0, 60.0, 58.3, 46.3, 16.3.
Anal. Calcd for C12H15NO2 (205.26): C, 70.22; H, 7.37; N, 6.83. Found: C, 70.44; H, 7.43, N, 7.32.
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(S)-4-Benzyl-3-isopropylmorpholin-2-one (2d). [α]D +24.5 (c 1.12, CHCl3); IR (neat) 3019, 2964,
1729 cm−1; 1H NMR (200 MHz, CDCl3) δ 7.30 (m, 5H), 4.29 (m, 2H), 3.94 (d, J = 13.6 Hz, 1H), 3.45 (d,
J = 13.6 Hz, 1H), 3.24 (d, J = 3.9 Hz, 1H), 2.86 (dt, J = 12.7, 2.9 Hz, 1H), 2.52 (ddd, J = 12.7, 2.9 Hz,
1H), 2.20 (m, 1H), 1.17 (d, J = 6.8 Hz, 3H), 1.10 (d, J = 6.8 Hz, 3H); 13C NMR (50 MHz, CDCl3) δ 169.2,
137.9, 128.5, 128.2, 127.3, 70.3, 67.1, 60.3, 46.8, 32.3, 19.9, 18.3. Anal. Calcd for C14H19NO2 (233.28):
C, 72.08; H, 8.20; N, 6.00. Found: C, 71.56; H, 8.23, N, 5.53.
(S)-4-Benzyl-3-isobutylmorpholin-2-one (2e). [α]D25 +34.2 (c 1.17, CHCl3); IR (neat) 2957, 1737, 1214,
755 cm−1; 1H NMR (200 MHz, CDCl3) δ 7.31 (m, 5 H), 4.35 (m, 2H), 3.95 (d, J = 13.2 Hz, 1H), 3.35 (d,
J = 13.2 Hz, 1H), 3.30 (t, J = 6.8 Hz, 1H), 2.94 (dt, J = 12.7, 4.4 Hz, 1H), 2.50 (dt, J = 12.7, 4.4 Hz, 1H),
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1.98 (m, 1H), 1.86 (t, J = 6.8 Hz, 2H), 0.95 (d, J = 6.8 Hz, 3H), 0.92 (d, J = 6.8 Hz, 3H); C NMR (50
MHz, CDCl3) δ 170.8, 137.3, 128.4, 127.5, 126.8, 67.0, 62.8, 58.6, 45.9, 39.6, 24.7, 23.0, 22.2; MSI m/z:
247 (M+).
(3S)-4-Benzyl-3-sec-butylmorpholin-2-one (2f). [α]D +28.7 (c 0.91, CHCl3); IR (neat) 3023, 1737, 758
1
cm−1; H NMR (200 MHz, CDCl3) δ 7.26 (m, 5H), 4.32 (m, 2H), 3.92 (d, J = 13.2 Hz, 1H), 3.79 (d, J =
13.2 Hz, 1H), 3.29 (d, J = 6.8 Hz, 1H), 2.54 (dt, J = 12.7, 4.8 Hz, 1H), 2.00 (m, 2H), 1.84 (m, 2H), 1.23
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(d, J = 6.3 Hz, 3H), 0.98 (t, J = 6.3 Hz, 3H); C NMR (50 MHz, CDCl3) δ 168.8, 139.6, 128.3, 127.8,
126.7, 68.6, 64.8, 60.4, 47.9, 37.6, 24.7, 21.0, 18.2; MSI m/z: 247 (M+).
(S)-4-Benzyl-3-(2-(methylthio)ethyl)morpholin-2-one (2g). [α]D25 +6.4 (c 1.10, CHCl3); IR (neat) 3027,
1
1730, 1151, 698 cm−1; H NMR (200 MHz, CDCl3) δ 7.28 (m, 5H), 4.47 (m, 2H), 3.90 (d, J = 13.2 Hz,
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1H), 3.72 (d, J = 13.2 Hz, 1H), 3.57 (m, 3H), 2.42 (m, 2H), 1.98 (q, J = 6.8 Hz, 2H), 1.97 (s, 3H); C
NMR (50 MHz, CDCl3) δ 170.2, 137.0, 128.8, 128.7, 128.1, 67.5, 63.3, 58.6, 46.9, 30.0, 29.3, 15.0; MSI
m/z: 265 (M+).
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(S)-4-Benzyl-3-phenylmorpholin-2-one (2h). [α]D +9.0 (c 1.06, CHCl3); IR (neat): 3025, 1737, 1216,
699 cm−1; 1H NMR (200 MHz, CDCl3) δ 7.29 (m, 10H), 4.64 (s, 1H), 4.47 (m, 2H), 3.76 (s, 2H), 3.51 (t,
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J = 5.9 Hz, 3H); C NMR (50 MHz, CDCl3) δ 171.3, 139.2, 136.4, 128.7, 128.6, 128.2, 128.0, 127.3,
126.4, 65.7, 63.7, 54.2, 28.4; MSI m/z: 267 (M+).
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(S)-4-Benzyl-3-(4-(benzyloxy)benzyl)morpholin-2-one (2i). [α]D −14.3 (c 1.05, CHCl3); IR (neat)
3024, 1734 cm−1; 1H NMR (200 MHz, CDCl3) δ 7.29 (m, 12 H), 7.17 (d, J = 7.1 Hz, 2H), 5.14 (s, 2H),