C. Salmi et al. / Tetrahedron 64 (2008) 4453e4459
4457
calcd C, 75.35; H, 8.96; N, 7.32. Found C, 75.32; H, 8.94; N,
7.31.
4.13. 3b-N-[Hydroxyethyl]amino-4-cholestene 29
Purification by column chromatography on silica gel using
1
CH2Cl2/MeOH/NH4OH(32%) 7:3:1 as eluent; viscous oil. H
4.8. 2-(1-Cyclopropyl-ethylamino)-e´thanol 13
NMR (300 MHz, CDCl3): d¼5.25 (s, 1H), 3.66e3.63 (m, 2H),
3.11e2.78 (m, 5H), 2.20e0.65 (m, 43H). 13C NMR (75 MHz,
CDCl3): d¼147.37, 122.37, 61.53, 56.57, 55.02, 54.78, 48.26,
52.87, 40.30, 39.90, 37.90, 36.78, 36.35, 36.17, 33.57, 32.87,
28.60, 28.40, 27.50, 24.62, 24.24, 23.21, 22.95, 21.55, 19.53,
19.05, 12.37. HRMS (FAB) m/z found 430.4006 [MþH]þ,
calcd for C29H51NO 430.4004.
Purification by column chromatography on silica gel using
1
methanol as eluent; clear oil. H NMR (300 MHz, CDCl3):
d¼0.08e0.91 (m, 5H), 1.17 (d, J¼6 Hz, 3H), 2.90e2.97 (m,
1H), 3.71 (t, J¼6 Hz, 2H), 4.19 (t, J¼6 Hz, 2H), 4.8 (s, 1H),
5.31 (s, 1H). 13C NMR (75 MHz, CDCl3): d¼2.78, 15.99,
18.87, 19.21, 44.04, 56.89, 62.62. C7H15NO calcd C, 65.07;
H, 11.70; N, 10.84. Found C, 65.10; H, 12.02; N, 10.65.
4.14. 3b-N-[Hydroxypropyl]amino-4-cholestene 30
Purification by column chromatography on silica gel using
1
CH2Cl2/MeOH/NH4OH(32%) 7:3:1 as eluent; viscous oil. H
4.9. 2-(1-Methyl-3-phenyl-allylamino)-e´thanol 17
NMR (300 MHz, CDCl3): d¼5.19 (s, 1H), 3.77e2.86 (m, 7H),
2.14e0.63 (m, 47H). 13C NMR (75 MHz, CDCl3): d¼147.13,
121.31, 63.80, 56.10, 54.52, 54.47, 46.13, 42.40, 39.82, 39.43,
37.42, 36.23, 36.08, 35.70, 33.08, 32.38, 30.99, 28.13, 27.92,
26.65, 24.15, 23.77, 22.75, 22.49, 21.08, 19.05, 18.59, 11.90.
HRMS (FAB) m/z found 444.4152 [MþH]þ, calcd for
C30H53NO 444.4161.
Purification by column chromatography on silica gel using
1
methanol as eluent; clear oil. H NMR (300 MHz, CDCl3):
d¼1.27 (d, J¼6 Hz, 3H), 2.40 (m, 2H), 2.74e2.86 (m, 1H),
3.39 (t, J¼6 Hz, 2H), 3.66e3.70 (m, 2H), 6.03e6.09 (dd,
J¼6, 15 Hz, 1H), 6.51 (d, J¼15 Hz, 1H), 7.21e7.40 (m,
5H). 13C NMR (75 MHz, CDCl3): d¼22.05, 48.73, 55.98,
61.29, 126.29; 127.41, 128.56, 130.14, 133.93, 136.96.
C12H17NO calcd C, 75.35; H, 8.96; N, 7.32. Found C,
75.25; H, 8.96; N, 7.14.
4.15. 3b-N-[Hydroxybutyl]amino-4-cholestene 31
Purification by column chromatography on silica gel using
1
CH2Cl2/MeOH/NH4OH(32%) 7:3:1 as eluent; viscous oil. H
4.10. 2-Cyclohexylamino-e´thanol 19
NMR (300 MHz, CDCl3): d¼5.23 (s, 1H), 3.56e2.63 (m, 8H),
2.16e0.62 (m, 46H). 13C NMR (75 MHz, CDCl3): d¼147.19,
121.37, 62.40, 56.21, 54.58, 54.31, 46.20, 42.47, 39.90, 39.59,
37.50, 36.30, 36.16, 35.83, 35.77, 33.16, 32.52, 32.43, 29.03,
28.20, 27.99, 26.75, 24.23, 23.85, 22.81, 22.56, 21.15, 19.15,
18.66, 11.97. HRMS (FAB) m/z found 458.4320 [MþH]þ,
calcd for C31H55NO 458.4317.
Purification by column chromatography on silica gel using
1
methanol as eluent; clear oil. H NMR (300 MHz, CDCl3):
d¼0.99e1.91 (m, 10H), 2.73 (t, J¼6 Hz, 2H), 3.40 (m, 2H),
3.62 (t, J¼6 Hz, 2H). 13C NMR (75 MHz, CDCl3): d¼25.05,
26.02, 33.26, 48.31, 56.77, 60.76. C10H21NO calcd C, 70.12;
H, 12.36; N, 8.18. Found C, 70.05; H, 12.34; N, 8.25.
4.16. 3b-N-[Hydroxypentyl]amino-4-cholestene 32
4.11. 2-(1,3-Dimethyl-butylamino)-e´thanol 21
Purification by column chromatography on silica gel using
1
CH2Cl2/MeOH/NH4OH(32%) 7:3:1 as eluent; viscous oil. H
Purification by column chromatography on silica gel using
1
methanol as eluent; clear oil. H NMR (300 MHz, CDCl3):
NMR (300 MHz, CDCl3): d¼5.30 (s, 1H), 4.64 (s, 2H), 3.64e
3.46 (m, 10H), 2.76e0.68 (m, 44H). 13C NMR (75 MHz,
CDCl3): d¼70.85, 56.07, 55.63, 50.48, 46.98, 46.06, 42.70,
41.19, 39.43, 39.27, 38.81, 37.78, 36.84, 36.73, 36.09,
35.77, 35.73, 31.65, 31.29, 31.24, 28.02, 27.95, 23.83,
23.64, 22.75, 22.47, 21.06, 18.55, 11.70, 11.59. HRMS
(FAB) m/z found 472.4479 [MþH]þ, calcd for C32H57NO
472.4474.
d¼0.82 (t, J¼6 Hz, 6H), 0.89 (d, J¼6 Hz, 3H), 1.05e1,29
(m, 1H), 1.55e1.64 (m, 1H), 2.59e2.74 (m, 4H), 3.27 (m,
2H), 3.57 (t, J¼6 Hz, 2H). 13C NMR (75 MHz, CDCl3):
d¼20.61, 22.76, 23.52, 25.26, 46.88, 48.96, 51.33, 60.99.
C8H19NO calcd C, 66.16; H, 13.19; N, 9.64. Found C,
66.05; H, 12.95; N, 9.59.
4.12. 2-(1,2,2-Trimethyl-propylamino)-e´thanol 23
4.17. 3b-N-[Hydroxyhexyl]amino-4-cholestene 33
Purification by column chromatography on silica gel using
1
methanol as eluent; clear oil. H NMR (300 MHz, CDCl3):
Purification by column chromatography on silica gel using
1
CH2Cl2/MeOH/NH4OH(32%) 7:3:1 as eluent; viscous oil. H
NMR (300 MHz, CDCl3): d¼5.23 (s, 1H), 3.60e3.56 (m, 2H),
3.12e0.63 (m, 56H). 13C NMR (75 MHz, CDCl3): d¼146.56,
122.07, 62.28, 56.23, 54.67, 46.56, 42.48, 39.93, 39.51, 37.54,
36.45, 36.17, 35.97, 35.78, 33.20, 32.69, 32.49, 30.25, 28.21,
d¼0.91 (s, 9H), 1.03 (d, J¼6 Hz, 3H), 1.75e2.17 (m, 2H),
2.24 (q, J¼6 Hz, 1H), 2.64e2.96 (m, 2H), 3.55e3.63 (m,
2H). 13C NMR (75 MHz, CDCl3): d¼15.45, 26.88, 34.83,
49.85, 61.37, 62.20. C8H19NO calcd C, 66.16; H, 13.19; N,
9.64. Found C, 66.54; H, 13.45; N, 9.78.