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E. Va´zquez et al. / Tetrahedron: Asymmetry 12 (2001) 2099–2102
(C-7); 28.61 (C-4); 44.84 (C-2); 61.69 (C-1%); 112.00 (C-5);
(C-5); 26.16 (C-4); 29.93 (C-9); 33.61 (C-3); 35.38 (C-8);
35.85 (C-4a); 37.40 (C-6); 43.78 (C-2); 59.51 (C-1%); 60.60
(C-8a); 126.58 (C-14); 127.00 (2C-10); 128.26 (2C-12);
146.83 (C-11); 212.64 (C-7). EI/MS: 285 (9); 270 (11); 256
(10); 228 (10); 215 (18); 214 (22); 105 (100); 104 (24); 103
(21); 79 (46); 77 (48); 42 (37). HRMS. C19H27NO. Calcd
285.2093 (M+), found 285.2077.
X-Ray analysis of 6. Crystallised from benzene/n-hexane.
Colourless, irregular crystal, 0.7×0.6×0.6 mm3,
C19H27NO, orthorhombic, P212121, a=6.3490(10), b=
126.80 (C-12); 127.30 (2C-10); 128.10 (C-6); 128.21 (2C-
11); 143.45 (C-9). HRMS. C15H21N. Calcd 215.1674 (M+),
found 215.1664.
15. Condensation of non-chiral enamine 1-benzyl-5-ethyl-
1,2,3,4-tetrahydropyridine with MVK led to a racemic
mixture of 1-benzyl-4a-ethyl-octahydroquinolin-7-one:
[h]2D0 0 in 90% overall yield.
16. Compound 5. Rf=0.32 (Al2O3/n-hexane:ethyl acetate=
92:8); (56.6%) pale yellow oil. IR (film, cm−1): 3050, 2934,
1713; [h]2D0 −98 (c 1.0, CH2Cl2); 1H NMR: l (ppm,
CDCl3): 0.72 (t, 3H-10, 7.70); 1.15–1.25 (m, 1H-4, 1H-3,
1H-9); 1.27 (d, 3H-2%, 6.60); 1.55–1.85 (m, 1H-3, 2H-5,
1H-4); 2.00–2.12 (m, 1H-6); 2.15 (hept, 1H-9, 7.70); 2.28–
2.45 (m, 1H-8, 1H-6, 1H-2); 2.61 (dd, 1H-8a, 4.40, 11.20);
2.75 (t, 1H-8, 11.70); 2.96 (dt, 1H-2, 3.30, 12.0); 3.55 (q,
1H-1%, 6.60); 7.20–7.40 (m, 5H, f-H); 13C NMR: l (ppm,
CDCl3): 7.50 (C-10); 21.72 (C-5); 22.47 (C-2%); 24.79 (C-5);
29.56 (C-9); 33.67 (C-3); 34.61 (C-8); 35.78 (C-4a); 37.15
(C-6); 41.11 (C-2); 59.58 (C-1%); 61.62 (C-8a); 126.90
(C-14); 127.27 (2C-12); 128.42 (2C-13); 145.25 (C-11);
212.80 (C-7). EI/MS: 285 (9); 270 (11); 256 (11); 228 (10)
215 (21); 214 (28); 105 (100); 104 (30); 103 (22); 79 (51);
77 (49); 42 (50). HRMS C19H27NO. Calcd 285.2093 (M+),
found 285.2077.
,
13.6643(17), c=19.468(3) A, Z=4. Bruker P4 diffrac-
tometer using Mo Ka radiation, T=298(2) K, 5058
reflections measured up to 2q=57.50°, 4264 independent
data (Rint=5.64%) for 3641 refined parameters. The struc-
ture was refined on basis on non absorption-corrected
data, using standard methods20 without neither restraints
nor constraints. Final R indices: R1=4.24% for 3641 data
having Fo>4| (Fo) and wR2=11.62% for all data. The
crystallographic data have been deposited in CDCC, UK
(deposition number 171160).
18. Jankowski, K.; Labrecque, D.; Jones, P.; Pare´, J. R.
Spectroscopy 1991, 9, 39–45.
19. Compound 7. Rf=0.30 (SiO2/CH2Cl2:MeOH=80:20); pale
yellow oil; IR (film, cm−1): 3325, 2936, 1714; [h]2D0 +27.6
1
(c 1.0, EtOH); H NMR: l (ppm, CDCl3): 0.93 (t, 3H-10,
17. Compound 6. Rf=0.40 (Al2O3/n-hexane:ethyl acetate=
92:8); (28.4%). Mp 76–78°C. IR (film, cm−1): 3050, 2933,
1711; [h]2D0 +5 (c 1.0, CH2Cl2); 1H NMR: l (ppm, CDCl3):
0.89 (t, 3H-10, 7.70); 1.21 (d, 3H-2%, 6.60); 1.30 (dt, 1H-4,
4.40, 13.56); 1.38 (dt, 1H-5, 4.40, 13.56); 1.48–1.65 (m,
1H-3, 1H-5, 1H-9); 1.77 (td, 1H-4, 4.40, 11.70); 1.93 (dt,
1H-3, 4.47, 13.56); 2.06 (hept, 1H-9, 7.70); 2.18–2.36 (m,
2H-2, 1H-6); 2.38 (dd, 1H-8, 1.83, 2.20); 2.45 (td, 1H-6,
6.23, 11.56); 2.86 (dd, 1H-8, 12.04); 3.15 (dd, 1H-8a, 4.40,
10.45); 3.54 (q, H-1%, 6.60); 7.15–7.40 (m, 5H, f-H); 13C
NMR: l (ppm, CDCl3): 7.45 (C-10); 19.48 (C-2%); 21.28
7.70); 1.27 (td, 1H-5, 4.77, 13.56); 1.40–150 (m, 1H-3,
1H-4, 1H-9); 1.59 (dt, 1H-5, 13.56); 1.62–1.71 (dt, 1H-4,
4.40, 13.20); 1.72–1.82 (sext, 1H-9, 7.70); 2.03 (dt, 1H-8,
15.04); 2.26 (dt, 2H-6, 2.56, 14.68); 2.40 (qd, 1H-3, 5.52);
2.58 (td, 1H-2, 3.30, 11.73); 2.76 (dd, 1H-8, 4.04, 14.85);
2.85 (broad signal, 1H-8a); 3.03 (dt, 1H-2, 1.84, 11.36);
13C NMR: l (ppm, CDCl3): 7.23 (C-10); 21.79 (C-4);
26.85 (C-3); 29.04 (C-9); 32.76 (C-5); 34.92 (C-4a); 37.19
(C-6); 44.67 (C-8); 47.27 (C-2); 62.59 (C-8a); 212.20 (C-7).
20. Sheldrick, G. M. SHELX97 Users Manual, University of
Go¨ttingen, Germany, 1997.