MAZGAROVA et al.
1328
(2H, Harom, J = 8.0 Hz), 7.73 d (1H, Harom, J = 8.0 Hz),
8.03 s (1H, CHO). Found, %: C 63.60; H 5.75; N 3.84;
S 8.84. C19H21NO4S. Calculated, %: C 63.49; H 5.89;
N 3.90; S 8.92.
evaporated, the residue was treated with 20 ml of
water, and the product was extracted into 50 ml of
chloroform. The extract was dried over MgSO4 and
evaporated under reduced pressure, and the residue
was subjected to column chromatography on silica gel
using petroleum ether–ethyl acetate (9:1) as eluent.
Yield 0.127 g (53%), amorphous powder, Rf 0.2 (petro-
Reaction of compound IIa with potassium
acetate. A solution of 0.455 g (1 mmol) of compound
IIa and 0.392 g (4 mmol) of potassium acetate in 5 ml
of DMF was heated for 4 h under reflux. The solvent
was removed under reduced pressure, the residue was
treated with 50 ml of methylene chloride and 30 ml of
water, and the organic phase was separated, washed
with water (20 ml), and dried over Na2SO4. The
solvent was removed under reduced pressure, and the
residue was subjected to column chromatography on
silica gel using benzene as eluent to isolate 0.193 g
(59%) of a mixture of compouds IV [9], V [9], and IX.
Further elution gave 0.041 g (11%) of a mixture of
acetates XIII and XIV at a ratio of 2:1.
1
leum ether–EtOAc, 9:1). H NMR spectrum (CDCl3),
δ, ppm: 0.45 d (3H, CH3, J = 7.0 Hz), 1.19 d (3H, CH3,
J = 6.3 Hz), 2.28 s (3H, CH3), 2.35 s (3H, CH3),
2.61 br.s (1H, OH), 2.84 d.q (1H, 3-H, J = 2.0, 7.3 Hz),
3.54 d.d (1H, 2-H, J = 2.0, 7.3 Hz), 3.82 quint (1H,
1′-H, J = 7.0 Hz), 6.82 s (1H, 4-H), 7.05 d (1H, Harom
J = 8.0 Hz), 7.18 d (2H, Harom, J = 8.3 Hz), 7.55 d (2H,
arom, J = 8.3 Hz), 7.62 d (1H, Harom, J = 8.0 Hz).
,
H
Found, %: C 65.98; H 6.65; N 3.99; S 9.20.
C19H23NO3S. Calculated, %: C 66.06; H 6.71; N 4.05;
S 9.28.
(1R*)-1-{(2R*,3R*)-3,5-Dimethyl-1-(4-methyl-
phenylsulfonyl)-2,3-dihydro-1H-indol-2-yl}ethyl
acetate (XIII). Rf 0.43 (C6H6). H NMR spectrum
(CDCl3), δ, ppm: 0.52 d (3H, CH3, J = 7.3 Hz), 1.15 d
(3H, CH3, J = 6.3 Hz), 2.00 s (3H, CH3), 2.25 s (3H,
CH3), 2.34 s (3H, CH3), 3.00 d.q (1H, 3-H, J = 2.0,
6.3 Hz), 3.80 d.d (1H, 2-H, J = 2.7, 5.0 Hz), 5.20 quint
(1H, 1′-H, J = 5.0, 7.3 Hz), 6.80 s (1H, 4-H), 7.05–
7.63 m (6H, Harom). Mass spectrum: m/z 387.15 [M]+.
C21H25NO4S. Calculated: M 387.1499.
REFERENCES
1
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phenylsulfonyl)-2,3-dihydro-1H-indol-2-yl}ethyl
1
acetate (XIV). Rf 0.43 (C6H6). H NMR spectrum
(CDCl3), δ, ppm: 0.50 d (3H, CH3, J = 7.1 Hz), 1.20 d
(3H, CH3, J = 6.5 Hz), 2.00 s (3H, CH3), 2.34 s (3H,
CH3), 2.80 d.q (1H, 3-H, J = 2.0, 6.5 Hz), 3.90 d.d
(1H, 2-H, J = 2.0, 4.3 Hz), 4.59 d.q (1H, 1′-H, J = 6.7,
4.3 Hz), 6.80 s (1H, 4-H), 7.05–7.63 m (6H, Harom).
Mass spectrum: m/z 387.15 [M]+. C21H25NO4S. Calcu-
lated: M 387.1499.
7. Sequeira, F.C., Bovino, M.T., Chipre, A.J., and
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phenylsulfonyl)-2,3-dihydro-1H-indol-2-yl}ethanol
(XV) with an impurity of isomer XVI. Compound
IV, 0.271 g (0.726 mmol), was added to a solution of
0.116 g (2.9 mmol) of sodium hydroxide in 6 ml of
ethanol. The progress of the reaction was monitored by
TLC. When the reaction was complete, the solvent was
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 9 2013