3340
R. N. Salvatore et al. / Tetrahedron 58 (2002) 3329±3347
4.1.31. Alkyl carbamate 4 (Table 5, entry 8). Yield 90%;
IR (thin ®lm) 3342, 3034, 2962, 2927, 1684, 1539, 1455,
1254, 1125, 969, 697 cm21; 1H NMR (CDCl3) d 4.47±4.49
(d, J8.4 Hz, 2H), 5.08 (s, 2H), 5.23 (bs, NH), 6.88±7.30
(m, 8H). 13C NMR (CDCl3) d 39.87, 66.88, 125.11, 125.75,
126.83, 128.11, 128.48, 136.30, 141.14, 156.02. Anal. calcd
for C13H13NO2S: C, 63.13; H, 5.30; N, 5.66; S, 12.97 Found:
C, 63.33; H, 5.87; N, 5.20; S, 12.78.
(s, 2H), 2.39 (m, 2H), 2.86 (m, 2H), 3.90 (m, 2H), 5.11 (bs,
NH), 6.99±7.08 (m, 5H). 13C NMR (90 MHz, CDCl3) d
13.62, 22.18, 26.04, 29.54, 30.36, 31.11, 31.71, 40.05,
63.46, 125.47, 127.94, 140.96, 156.42. Anal. calcd for
C16H25NO2: C, 72.96; H, 9.57; N, 5.32. Found: C, 72.89;
H, 9.57; N, 5.33.
4.1.38. Alkyl carbamate 4 (Table 6, entry 6). Yield 82%;
clear yellow oil. IR (thin ®lm) 3326, 3061, 3026, 2920,
1
4.1.32. Alkyl carbamate 4 (Table 5, entry 9). Yield 85%;
oil; IR (thin ®lm) 3317, 3061, 3025, 2942, 2857, 1701, 1428,
2855, 1695, 1529, 1497, 1452, 1312, 1246, 1051 cm21; H
NMR (CDCl3) d 1.26±1.67 (m, 14H), 1.71±1.78 (m, 2H),
2.47 (t, J7.5 Hz, 2H), 2.28 (m, 1H), 3.89 (t, J6.5 Hz,
2H), 7.00±7.13 (m, 6H). 13C NMR (CDCl3) d 23.42,
25.26, 27.09, 30.62, 32.08, 32.20, 50.80, 63.80, 125.77,
128.25, 141.33, 155.60. Anal. calcd for C18H27NO2: C,
74.14; H, 9.15; N, 5.09. Found: C, 74.13; H, 9.46; N, 4.90.
1
1296, 1227, 1121, 1013, 933, 747, 699 cm21; H NMR
(CDCl3) d 2.02 (q, J7.0 Hz, 2H), 2.74 (t, J7.6 Hz,
2H), 2.86 (bs, 2H), 3.69 (bs, 2H), 4.18 (t, J6.5 Hz, 2H),
4.61(d, 2H, J13.0 Hz), 7.13±7.32 (m, 10H). 13C NMR
(CDCl3) d 30.60, 32.32, 45.61, 64.86, 125.92, 126.28,
126.45, 128.78, 141.39, 155.65.
4.1.39. Alkyl carbamate 4 (Table 6, entry 7). Yield 88%;
yellow oil; IR (thin ®lm) 3330, 2949, 2870, 1719, 1538,
4.1.33. Alkyl carbamate 4 (Table 6, entry 1). Yield 87%;
IR (thin ®lm) 3330, 3085, 3062, 3027, 2949, 2859, 1699,
1
1454, 1248, 1149, 1082, 1024, 747, 700 cm21; H NMR
1
1524, 1496, 1453, 1256, 1138 cm21; H NMR (CDCl3) d
(CDCl3) d 1.34±1.39 (m, 2H), 1.68±1.80 (m, 4H), 2.49 (t,
J7.3 Hz, 2H), 2.90±2.98 (m, 1H), 3.22±3.27 (m, 1H),
3.55±3.91(m, 5H), 5.04 (bs, N H), 6.98±7.11 (m, 5H). 13C
NMR (CDCl3) d 25.82, 28.40, 30.66, 32.12, 44.75, 64.20,
68.07, 76.79, 125.0, 128.37, 141.39, 156.86. Anal. calcd for
C15H21NO3: C, 68.42; H, 8.04; N, 5.32. Found: C, 68.78; H,
8.57; N, 5.32.
1.96 (m, 2H), 2.70 (t, J7.5 Hz, 2H), 4.14 (t, J6.5 Hz,
2H), 4.38 (d, J5.8 Hz, 2H), 5.04 (bs, NH), 7.18±7.39
(m, 10H). 13C NMR (CDCl3) d 30.63, 32.11, 45.01, 64.38,
125.90, 127.43, 128.36, 128.62, 138.54, 141.33, 156.62.
Anal. calcd for C17H19NO2: C, 75.81; H, 7.11; N, 5.20.
Found: C, 75.27; H, 7.42; N, 5.05.
4.1.34. Alkyl carbamate 4 (Table 6, entry 2). Yield 93%;
IR (thin ®lm) 3324, 3061, 3027, 2972, 1698, 1532, 1453,
1328, 1245, 1061, 748, 699 cm21; 1H NMR (CDCl3) d 1.50
(d, J6.7 Hz, 3H), 1.93 (m, 2H), 2.68 (m, 2H), 4.06±4.11
(m, 2H), 4.82 (m, 1H), 4.98 (m, 1H), 7.17±7.38 (m, 10H).
13C NMR (CDCl3) d 22.41, 30.61, 32.10, 50.51, 64.23,
125.87, 127.24, 128.34, 128.59, 141.35, 143.58, 155.77.
Anal. calcd for C18H11NO2: C, 76.29; H, 7.47; N, 4.94.
Found: C, 75.56; H, 7.53; N, 4.92.
4.1.40. Alkyl carbamate 4 (Table 6, entry 8). Yield 90%;
IR (thin ®lm) 3328, 3105, 3083, 3061, 3025, 2948, 2860,
1700, 1517, 1453, 1327, 1246, 1130 cm21 1H NMR
;
(CDCl3) d 2.01(m, 2H), 2.73 (t, J7.5 Hz, 2H), 4.17 (t,
J6.5 Hz, 2H), 4.55 (s, 2H), 5.52 (bs, NH), 6.97±7.36 (m,
8H). 13C NMR (CDCl3) d 30.35, 31.80, 39.48, 64.12,
124.69, 125.36, 125.67, 126.23, 128.12, 141.04, 141.39,
156.19.
4.1.41. Alkyl carbamate 4 (Table 6, entry 9). Yield 82%;
IR (thin ®lm) 3330, 3147, 3318, 3084, 3061, 3026, 2951,
4.1.35. Alkyl carbamate 4 (Table 6, entry 3). Yield 90%;
pale yellow oil; IR (thin ®lm) 3335, 3061, 3026, 2943, 2862,
1716, 1539, 1454, 1250, 1139, 1030, 910, 844, 743,
1
2861, 1705, 1602, 1524, 1453, 1327, 1247 cm21; H NMR
(CDCl3) d 1.96 (m, 2H), 2.68 (t, J7.5 Hz, 2H), 4.12 (t,
J6.5 Hz, 2H), 4.35 (d, 2H, J5.3 Hz) 5.06 (bs, NH), 6.24
(s, 1H), 6.32±6.33 (s, 1H), 7.17±7.36 (m, 6H). 13C NMR
(CDCl3) d 30.36, 31.83, 37.72, 64.19, 106.88, 110.14,
125.69, 128.14, 141.08, 141.83, 151.58, 156.31.
1
699 cm21; H NMR (CDCl3) d 1.96 (m, 2H), 2.70 (t, J
7.5 Hz, 2H), 4.14 (t, J6.5 Hz, 2H), 4.38 (d, J5.8 Hz, 2H),
5.04 (bs, NH), 7.18±7.39 (m, 10H). 13C NMR (90 MHz,
CDCl3) d 30.63, 32.11, 36.13, 42.08, 64.17, 125.90,
127.43, 128.36, 128.62, 138.54, 141.33, 156.62. Anal.
calcd for C18H11NO2: C, 76.29; H, 7.47; N, 4.94. Found:
C, 75.53; H, 7.55; N, 4.89.
4.1.42. Alkyl carbamate 4 (Table 6, entry 10). Yield 89%;
IR (thin ®lm) 3413, 3330, 3058, 3025, 2942, 2855, 1697,
1
1520, 1455, 1338, 1257, 1082 cm21; H NMR (CDCl3) d
4.1.36. Alkyl carbamate 4 (Table 6, entry 4). Yield 85%;
yellow oil; IR (thin ®lm) 3323, 3062, 3029, 2959, 2941,
2866, 2836, 1680, 1611, 1537, 1512, 1468, 1298, 1246,
2.40 (m, 2H), 2.84 (m, 2H), 3.14 (m, 2H), 3.60 (m, 2H), 4.24
(m, 2H), 4.94 (brs, NH), 7.01±8.60 (m, 9H). 13C NMR
(CDCl3) d 25.85, 30.72, 32.20, 41.39, 64.31, 111.42,
112.67, 118.75, 119.41, 122.12, 122.30, 126.03, 127.37,
128.50, 136.51, 141.47, 156.93. Anal. calcd for
C20H22N2O2: C, 74.51; H, 6.88; N, 8.69. Found: C, 74.44;
H, 6.66; N, 8.23.
1
1032 cm21; H NMR (CDCl3) d 1.93±1.95 (m, 2H), 2.66
(t, J7.4 Hz, 2H), 2.77 (t, J6.7 Hz, 2H), 3.42 (m, 2H),
3.79 (s, 3H), 4.1(m, 2H), 4.69 (bs, N H), 6.83±7.38 (m,
9H). 13C NMR (CDCl3) d 30.66, 32.14, 35.20, 42.29,
55.24, 64.17, 114.02, 125.92, 128.39, 129.71, 130.79,
141.40, 156.58, 158.25.
4.1.43. Aromatic carbamate 4 (Table 7, entry 1). Yield
98%; oil; IR (thin ®lm) 3317, 3061, 3035, 2988, 2945, 2892,
4.1.37. Alkyl carbamate 4 (Table 6, entry 5). Yield 91%;
colorless oil; IR (thin ®lm) 3336, 3062, 3026, 2954, 2929,
1693, 1597, 1532, 1444, 1313, 1227 cm21 1H NMR
;
(CDCl3) d 5.04 (s, 2H), 6.75±7.34 (m, 10H). 13C NMR
(CDCl3) d 66.88, 118.63, 123.39, 126.89, 127.51, 128.51,
128.94, 135.95, 137.71, 153.37.
1
2857, 1697, 1535, 1454, 1249, 1142, 1030 cm21; H NMR
(CDCl3) d 0.72 (t, J6.87 Hz, 3H), 1.12±1.30 (m, 8H), 1.74