NEW SYNTHESIS OF (ꢀ)-CHERYLLINE
2237
IR (KBr, cmꢄ1): 3435, 2788, 1509, 1258; mass for C18H21NO3 [M þ 1] 300.2; 1H NMR
(400 MHz, DMSO) (d ppm): 2.25 (3H, s, -N-CH3), 2.42 (1H, m, CH-CH2-N), 2.78 (1H,
m, CH-CH2-N), 3.32 (2H, s,(br), Ar-CH2-N), 3.45 (3H, s, OCH3), 3.49 (3H, s, OCH3),
3.98 (1H, t, J ¼ 6.0 Hz Ar-CH-Ar), 6.27 (1H, s, Ar), 6.62 (1H, s, Ar), 6.65 (2H, d,
J ¼ 4.45 Hz, Ar), 6.95 (2H, d, J ¼ 8.36 Hz, Ar), 9.17 (1H, s, Ar-OH);13C NMR
(100 MHz, DMSO) (d ppm): 44.06, 45.97, 55.72, 55.76, 57.85, 61.80, 109.70, 112.48,
115.21, 127.64, 129.44, 129.88, 135.89, 147.45,147.50, 155.98.
General Procedure for the Synthesis of 4-f1-(4-Benzyloxy-3-
methoxy-phenyl)-2-[(1-ethoxy-vinyl)-methyl-amino]-ethylg-
phenol (24)
BF3 ꢁ OEt2 (47%) (15 g, 0.051 mol) was added over 25 min to a stirred solution
of [2-(4-benzyloxy-3-methoxy-phenyl)-2-phenoxy-ethyl]-methyl-carbamic acid ethyl
ester (23) (15 g, 0.0344 mol) and ethyl acetate (150 mL) at 0–5 ꢂC. The reaction
mixture was allowed to room temperature and stirred for 2 h. After completion of
the reaction by TLC, the reaction mixture was poured into DM water (100 ml)
and the solution was extracted with ethyl acetate (2 ꢃ 100 mL). Combined organic
extracts were dried over sodium sulfate, filtered, and concentrated under reduced
pressure to get 15 g of crude product. Purification of crude product was achieved
by column chromatography using 10% ethyl acetate in hexane as an eluent gave
yellow color oil (5.5 g, 55%) (24); IR (KBr, cmꢄ1): 3333, 3015, 1673, 1407; mass
1
for C26H29NO5 [M þ 1] 436.5; H NMR (400 MHz, DMSO) (d ppm): 1.11 (3H, s,
OCH2-CH3), 2.6 (3H, s, N-CH3), 3.38 (1H, s, CH-HCH-N), 3.73 (4H, m,
CH-HCH-N and OCH3), 4.02 (1H, t, J ¼ 7.6 Hz, Ar-CH-Ar), 5.04 (2H, s, CH2-Ph),
6.69 (2H, d, J ¼ 7.64 Hz, Ar), 6.76 (1H, d, J ¼ 8.0 Hz, Ar), 6.88 (1H, s, Ar), 6.93 (1H,
d, J ¼ 7.6 Hz, Ar), 7.10 (2H, d, J ¼ 8.32 Hz, Ar), 7.28–7.42 (5H, m, Ar), 9.23 (1H, s,
Ar-OH); 13C NMR (100 MHz, DMSO) (d ppm): 13.3, 34.7, 41.0, 56.3, 57.2, 60.4,
78.2, 115.6, 116.2, 121.7, 127.3, 127.4, 128.7, 129.8, 135.6, 136.3, 140.9, 145.1,
148.1, 154.8, 156.2. Anal. calcd. for C26H29NO5: C, 71.70; H, 6.71; N, 3.32. Found:
C, 71.68; H, 6.69; N, 3.28.
ACKNOWLEDGMENT
We thank Suven Life Sciences for the excellent analytical facilities and allowing
us to publish these results.
SUPPORTING INFORMATION
1
Full experimental detail and H and 13C NMR spectra for this article can be
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