SHINKEVICH et al.
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3.80–3.85 m (2H), 6.54–6.63 m (4H), 7.29–7.44 m
(6H), 7.54–7.57 m (2H), 7.71–7.75 m (1H). C NMR
Compound XVIII. Yield 60 mg (43%), mp 150–
152°C (from Et2O). IR spectrum (CHCl3), ν, cm–1:
1695, 1740 (C=O); 3310 (NH). H NMR spectrum
13
1
spectrum (CDCl3), δC, ppm: 22.9, 46.5, 50.7, 55.5,
70.3 (CPh), 110.6, 114.1, 114.7, 120.2, 124.0, 124.8,
127.3, 127.8, 127.9, 139.8, 140.8, 141.2, 150.7, 151.2,
168.4 (C=N). Found, %: C 71.88; H 5.03; N 5.03.
C17H14ClNO. Calculated, %: C 71.96; H 4.97; N 4.94.
(CDCl3), δ, ppm: 1.82–1.95 m (2H, CH2), 2.04 s (3H,
CH3), 2.14–2.24 m (1H), 2.42–2.52 m (1H), 4.10–
4.14 m (2H), 6.75–6.78 m (1H), 6.88–7.03 m (2H),
7.10–7.14 m (1H), 7.27–7.29 m (3H), 7.49–7.52 m
(2H), 9.23 s (1H, NH). 13C NMR spectrum (CDCl3),
δC, ppm: 20.9 (CH3), 23.3 (CH2), 36.6 (CH2), 64.3
(CH2O), 84.2 (CPh), 115.5, 117.4, 122.4, 124.1, 125.4,
126.1, 128.1, 128.4, 138.7, 143.0, 167.5 (C=O), 171.1
(C=O). Found, %: C 70.17; H 5.88; N 4.14.
C19H19NO4. Calculated, %: C 70.14; H 5.89; N 4.30.
2-(1-Isobutyl-2-phenylpyrrolidin-2-yl)-1,3-benz-
oxazole (XVe). Yield 60 mg (30%). IR spectrum
1
(CHCl3): ν 1610 cm–1 (C=N). H NMR spectrum
(CDCl3), δ, ppm: 0.81 d (3H, CH3, J = 6.7 Hz), 1.10 d
(3H, CH3, J = 6.7 Hz), 1.75–1.87 m (1H), 1.95–2.09 m
(3H), 2.18–2.28 m (1H), 2.44 q (1H, J = 9.3 Hz), 2.55 t
(1H, J = 11.8 Hz), 3.05–3.10 m (1H), 3.38–3.45 m
(1H), 7.29–7.43 m (7H), 7.51–7.54 m (1H), 7.80–
7.83 m (1H). 13C NMR spectrum (CDCl3), δC, ppm:
20.3 (CH3), 21.4 (CH3), 22.0 (CH2), 27.5 (CH), 50.2
(CH2), 57.9 (CH2), 71.9 (CPh), 110.8, 120.2, 124.1,
124.7, 126.8, 127.2, 128.1, 140.7, 143.2, 150.7, 167.5
(C=N). Mass spectrum (CI, NH3), m/z (Irel, %): 322
(23) [M + 2]+, 321 (100) [M + H]+, 274 (4) [M –
CH(CH3)2]+. Found: [M + H]+ 321.1961. C21H25N2O.
Calculated: [M + H]+ 321.1961.
We gratefully acknowledge the Russian Foundation
for Basic Research (project no. 05-03-33 257) and the
Bilateral Scientific Cooperation program of the Russian
Foundation for Basic Research and the Government of
Flanders (project no. 05-03-34 811) for support of this
research.
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2-(3-Hydroxypropyl)-2-phenyl-2H-1,4-benzoxa-
zin-3(4H)-one (XVII) and 3-(3-oxo-2-phenyl-3,4-
dihydro-2H-1,4-benzoxazin-2-yl)propyl acetate
(XVIII). A mixture of 130 mg (0.431 mmol) of amide
Vb, 0.13 g (2.32 mmol) of potassium hydroxide, and
5 ml of methanol was heated for 1 h under reflux. The
precipitate was filtered off, the solvent was removed
from the filtrate under reduced pressure, and the
residue was treated with water and extracted with ethyl
acetate. The extract was washed with water and a satu-
rated solution of sodium chloride and dried over
Na2SO4. The solvent was removed under reduced pres-
sure, and the residue was subjected to column chroma-
tography using hexane–ethyl acetate as eluent to iso-
late compounds XVII and XVIII.
2. Harrowven, D.C. and Pattenden, G., Comprehensive
Organic Synthesis: Selectivity, Strategy, and Efficiency
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Compoundd XVII. Yield 60 mg (49%), mp 134–
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135°C (from Et2O). IR spectrum (CHCl3), ν, cm–1:
1
1700 (C=O), 3405 (NH), 3630 (OH). H NMR spec-
trum (CDCl3), δ, ppm: 1.79–1.91 m (3H, CH2, OH),
2.15–2.24 m (1H), 2.47–2.57 m (1H), 3.67–3.71 m
(2H), 6.72–6.75 m (1H), 6.86–6.92 m (1H), 6.97–
7.02 m (1H), 7.11–7.14 m (1H), 7.23–7.31 m (3H),
7.48–7.51 m (2H), 8.91 s (1H, NH). 13C NMR spec-
trum (CDCl3), δC, ppm: 27.3 (CH2), 36.3 (CH2), 62.5
(CH2OH), 84.5 (CPh), 115.5, 117.4, 122.4, 124.2,
125.4, 126.1, 128.1, 128.4, 138.9, 143.1, 167.6 (C=O).
Found, %: C 72.17; H 6.18; N 4.96. C17H17NO3. Cal-
culated, %: C 72.07; H 6.05; N 4.94.
13. Sudau, A., Munch, W., Bats, J.W., and Nubbemeyer, U.,
Chem. Eur. J., 2001, vol. 7, p. 611.
14. Hodgson, D.M. and Robinson, L.A., Chem. Commun.,
1999, p. 309.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 43 No. 7 2007