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3.1.5. (R)-3-Ethoxycarbonyl-1-thia-4-azaspiro[4.4]nonane 2b4
Light yellow oil; yield: 53%; [h]1D9=−136 (c=1.2, ethyl acetate); bp >230°C (dec.); H NMR
(200 MHz, CDCl3): l 4.24 (dq, J=1.8, 7.2 Hz, 2H), 3.92 (dd, J=7.2, 9.2 Hz, 1H), 3.39 (dd,
J=7.2, 10.4 Hz, 1H), 2.98 (dd, J=9.4, 10.0 Hz, 1H), 2.51 (s, 1H), 1.78–2.17 (m, 8H), 1.31 (t,
J=7.2 Hz, 3H); IR (film): 3302, 2962, 1739, 1446, 1370, 1335, 1224, 1116, 1027, 831 cm−1. Calcd
for C10H17NO2S: C, 55.78; H, 7.96; N, 6.51. Found: C, 55.58; H, 7.86; N, 6.59. MS (EI): m/z
(relative intensity) 114 (44), 142 (93), 168 (59), 186 (100), 215 (M+, 76).
1
3.1.6. (R)-3-(1-Methylethoxy)carbonyl-1-thia-4-azaspiro[4.4]nonane 2c
1
Light yellow oil; yield: 61%; [h]1D8=−124 (c=1.2, ethyl acetate); bp >230°C (dec.); H NMR
(200 MHz, CDCl3): l 5.10 (m, 1H), 3.90 (dd, J=7.2, 9.2 Hz, 1H), 3.38 (dd, J=7.2, 10.4 Hz,
1H), 2.96 (dd, J=9.2, 10.2 Hz, 1H), 2.54 (s, 1H), 1.73–2.31 (m, 8H), 1.28 (dd, J=2.6, 6.0 Hz,
6H); IR (film): 3303, 2962, 1735, 1450, 1361, 1325, 1227, 1169, 1107, 822 cm−1. Calcd for
C11H19NO2S: C, 57.61; H, 8.35; N, 6.11. Found: C, 57.81; H, 8.40; N, 5.88. MS (EI): m/z
(relative intensity) 114 (25), 142 (100), 182 (11), 200 (41), 229 (M+, 43).
3.1.7. (R)-3-Methoxycarbonyl-1-thia-4-azaspiro[4.5]decane 3a
Colorless oil; yield: 51%; [h]2D0=−138 (c=1.0, ethyl acetate); bp 234–236°C; H NMR (200
1
MHz, CDCl3): l 4.07 (dd, J=6.8, 9.4 Hz, 1H), 3.79 (s, 3H), 3.30 (dd, J=6.6, 10.4 Hz, 1H), 2.88
(dd, J=9.6, 10.4 Hz, 1H), 2.43 (s, 1H), 1.29–1.91 (m, 10H); IR (film): 3300, 2931, 1744, 1437,
1348, 1232, 1199, 1157, 878, 802 cm−1. Calcd for C10H17NO2S: C, 55.78; H, 7.96; N, 6.51.
Found: C, 55.88; H, 7.99; N, 6.48. MS (EI): m/z (relative intensity) 41 (98), 59 (100), 156 (23),
168 (38), 172 (49), 215 (M+, 25).
3.1.8. (R)-3-Ethoxycarbonyl-1-thia-4-azaspiro[4.5]decane 3b4
1
Colorless oil; yield: 58%; [h]2D0=−142 (c=1.5, ethyl acetate); bp 248–250°C; H NMR (200
MHz, CDCl3): l 4.26 (dq, J=2.0, 7.2 Hz, 2H), 4.04 (dd, J=6.6, 9.6 Hz, 1H), 3.30 (dd, J=6.6,
10.4 Hz, 1H), 2.87 (dd, J=9.6, 10.2 Hz, 1H), 2.43 (s, 1H), 1.46–1.91 (m, 10H), 1.31 (t, J=7.2
Hz, 3H); IR (film): 3301, 2932, 1739, 1447, 1371, 1341, 1191, 1157, 1026, 880, 800 cm−1. Calcd
for C11H19NO2S: C, 57.61; H, 8.35; N, 6.11. Found: C, 57.48; H, 8.76; N, 6.30. MS (EI): m/z
(relative intensity) 156 (73), 182 (84), 186 (100), 229 (M+, 82).
3.1.9. (R)-3-(1-Methylethoxy)carbonyl-1-thia-4-azaspiro[4.5]decane 3c
1
Colorless oil; yield: 54%; [h]2D0=−144 (c=1.2, ethyl acetate); bp >252°C (dec.); H NMR (200
MHz, CDCl3): l 5.10 (m, 1H), 4.01 (dd, J=6.6, 9.4 Hz, 1H), 3.29 (dd, J=6.4, 10.2 Hz, 1H),
2.84 (dd, J=9.4, 10.0 Hz, 1H), 2.44 (s, 1H), 1.46–1.92 (m, 10H), 1.28 (dd, J=3.4, 6.2 Hz, 6H);
IR (film): 3301, 2932, 1736, 1448, 1362, 1232, 1194, 1158, 1107, 878, 801 cm−1. Calcd for
C12H21NO2S: C, 59.22; H, 8.70; N, 5.76. Found: C, 59.03; H, 8.75; N, 5.82. MS (EI): m/z
(relative intensity) 156 (14), 196 (20), 200 (55), 243 (M+, 100).
3.1.10. (R)-3-Methoxycarbonyl-1-thia-4-azaspiro[4.6]undecane 4a
Colorless oil; yield: 67%; [h]2D0=−124 (c=1.8, ethyl acetate); bp 240–242°C; H NMR (200
1
MHz, CDCl3): l 4.02 (dd, J=6.6, 9.2 Hz, 1H), 3.78 (s, 3H), 3.34 (dd, J=6.8, 10.6 Hz, 1H), 2.91
(dd, J=9.6, 10.6 Hz, 1H), 2.48 (s, 1H), 1.58–2.15 (m, 12H); IR (film): 3305, 2928, 2855, 1744,
1437, 1345, 1220, 1170, 1007, 942, 850, 790 cm−1. Calcd for C11H19NO2S: C, 57.61; H, 8.35; N,
6.11. Found: C, 57.57; H, 8.05; N, 6.14. MS (EI): m/z (relative intensity) 95 (60), 112 (78), 170
(60), 172 (100), 182 (90), 196 (94), 229 (M+, 71).