HETEROCYCLES, Vol. 78, No. 2, 2009
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hexane/EtOAc (1 : 1) to afford pure product (4a-d) as a viscous oil.
(2S, 1'R)-N-(2'-Methoxy-1'-phenylethyl)-2-acetoxypropylamine (4a).
[α]D -56.67 (c 1.09, CHCl3). 1H NMR (270 MHz, CDCl3): δ = 1.19 (d, J = 6.3Hz, 3H), 2.04 (s, 3H), 2.10
(brs, 1H), 2.46 (dd, J = 4.6, 12.2Hz, 1H), 2.65 (dd, J = 7.7, 12.2Hz, 1H), 3.33-3.45 (m, 2H), 3.37 (s, 3H),
3.87 (dd, J = 4.1, 9.1Hz, 1H), 4.89-4.96 (m, 1H), 7.24-7.39 (m, 5H). 13C NMR (67.8 MHz, CDCl3): δ =
170.15, 140.28, 128.03, 127.26, 127.20, 77.49, 70.82, 62.48, 58.37, 51.70, 20.92, 17.74. IR (film): 3340,
2980, 2931, 2890, 2821, 1740, 1478, 1371, 1240, 1109 cm-1. MS m/z: CI, 252 (M++1). Anal. Calcd for
C14H21NO3HCl: C, 58.43; H, 7.70; N, 4.86. Found: C, 58.21; H, 7.74; N, 4.99. HCl salt: colorless crystal,
mp 100°C (Et2O).
(2S, 1'R)-N-(2'-Methoxy-1'-phenylethyl)-2-acetoxybutylamine (4b).
[α]D -71.02 (c 0.98, CHCl3). 1H NMR (270 MHz, CDCl3): δ = 0.83 (t, J = 7.5Hz, 3H), 1.49-1.67 (m, 2H),
2.02 (brs, 1H), 2.05 (s, 3H), 2.52 (dd, J = 4.9, 12.3Hz, 1H), 2.63 (dd, J = 7.0, 12.3Hz, 1H), 3.32-3.44 (m,
13
2H), 3.36 (s, 3H), 3.86 (dd, J = 4.2, 9.0Hz, 1H), 4.83-4.88 (m, 1H), 7.25-7.39 (m, 5H). C NMR (67.8
MHz, CDCl3): δ = 170.71, 140.50, 128.27, 127.46. 127.38, 77.68, 75.43, 62.77, 58.64, 49.88, 25.04,
21.16, 9.34. IR (film): 3340, 2970, 2935, 2880, 2821, 1740, 1458, 1371, 1240, 1110 cm-1. MS m/z: CI,
266 (M++1). Anal. Calcd for C15H23NO3HCl: C, 59.69; H, 8.01; N, 4.64 Found: C, 59.47; H, 8.01; N, 4.59.
HCl salt: colorless crystal, mp 105°C (Et2O).
(2S, 1'R)-N-(2'-Methoxy-1'-phenylethyl)-2-acetoxypentylamine (4c).
[α]D -62.99 (c 1.17, CHCl3). 1H NMR (270 MHz, CDCl3): δ = 0.87 (t, J = 7.3Hz, 3H), 1.22-1.35 (m, 2H),
1.48-1.57 (m, 2H), 2.00 (brs, 1H), 2.05 (s, 3H), 2.52 (dd, J = 4.8, 12.4Hz, 1H), 2.63 (dd, J = 7.0, 12.4Hz,
1H), 3.34-3.45 (m, 2H), 3.37 (s, 3H), 3.86 (dd, J = 4.3, 8.9Hz, 1H), 4.88-4.97 (m, 1H), 7.23-7.39 (m, 5H).
13C NMR (67.8 MHz, CDCl3): δ = 170.02, 140.27, 127.93, 127.14, 127.03, 77.37, 73.68, 62.46, 58.19,
50.10, 33.99, 20.61, 18.02, 13.48. IR (film): 3340, 2960, 2931, 2871, 2821, 1740, 1459, 1378, 1240, 1110
cm-1. MS m/z: CI, 280 (M++1). Anal. Calcd for C16H25NO3: C, 68.79; H, 9.02; N, 5.01. Found: C, 68.60;
H, 9.08; N, 5.04.
(2S, 1'R)-N-(2'-Methoxy-1'-phenylethyl)-2-acetoxy-3-methylbutylamine (4d).
[α]D -62.02 (c 1.22, CHCl3). 1H NMR (270 MHz, CDCl3): δ = 0.82 (d, J = 6.8Hz, 3H), 0.86 (d, J = 6.8Hz,
3H), 1.75 (brs, 1H), 1.83-1.99 (m, 1H), 2.07 (s, 3H), 2.56 (dd, J = 4.8, 12.4Hz, 1H), 2.61 (dd, J = 6.9,
12.4Hz, 1H), 3.32-3.44 (m, 2H), 3.36 (s, 3H), 3.84 (dd, J = 4.2, 9.0Hz, 1H), 4.77-4.83 (m, 1H), 7.22-7.39
(m, 5H). 13C NMR (67.8 MHz, CDCl3): δ = 170.42, 140.36, 128.03, 127.24, 127.14, 78.13, 77.47, 62.68,
58.35, 47.84, 29.45, 20.67, 18.29, 17.04. IR (film): 3340, 2961, 2930, 2880, 2822, 1738, 1453, 1372,
1240, 1110 cm-1. MS m/z: CI, 280 (M++1). Anal. Calcd for C16H25NO3: C, 68.79; H, 9.02; N, 5.01.
Found: C, 68.64; H, 8.95; N, 5.08.
General procedure for the ring-opening reaction of aziridine with benzyl bromide.