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RSC Advances
Page 4 of 5
DOI: 10.1039/C6RA02792J
COMMUNICATION
Journal Name
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crude compound was dissolved in 50% methanol/chloroform
and passed through neutral alumina, afforded colorless
liquid compound 7 in 91% yield.
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270.
Yield: 90%, Light brown colour liquid;
[α]
25 = +88.8 (c 1,
D
MeOH); 1H NMR (400 MHz, Chloroform-d) δ 9.84 (s, 1H),
7.72 (t, J = 2.0 Hz, 1H), 7.17 (t, J = 2.0 Hz, 1H), 5.41 (d, J = 4.8
Hz, 1H), 4.61 (d, J = 4.8 Hz, 1H), 4.51 (d, J = 3.6 Hz, 1H), 4.30
(dd, J = 11.2, 4.8 Hz, 1H), 4.20 (d, J = 11.2 Hz, 1H), 4.00 (s,
3H), 3.98 (dd, J = 4.8, 3.2 Hz, 1H), 3.46 (s, 3H), 3.44 (s, 3H);
13C NMR (100 MHz, Chloroform-d) δ 137.50, 122.69, 121.37,
103.66, 85.67, 78.69, 70.92, 68.34, 55.99, 55.55, 36.91;
HRMS (ESI) exact calculated mass for [M+]
4
5
(C11H19O4N2)requires m/z 243.1339, found m/z 243.1336; LR-
MS (ESI) ES+: 243.2, ES-: 126.9.
15 The racemic Mosher’s acid silver salt (4.6 mg, 0.013 mmol)
was mixed with CCIL 7 (10 mg, 0.027 mmol) in 0.6 mL of
6
7
(a) K. Fukumoto, M. Yoshizawa and H. Ohno, J. Am. Chem.
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CD3CN and stirred for 10 min at room temperature to
exchange anions. The formed AgI precipitate was filtered
and filtrate was analyzed by 19F NMR (376.5 MHz). For CCILs
8-11, the racemic salt (1 equiv.) was mixed with each CIL (10
mg, 2equiv.) separately in dry ACN and stirred for 10 min.
Filtered the formed salts and concentrated the filtrate under
reduced pressure using rotary evaporator. The residual
compound was dissolved in CDCl3 and analyzed by 19F NMR.
16 Effect of CCIL
each time different concentrations of CCIL
6 eq) was mixed with racemic salt and studied the effect of
concentration of CCIL
for chiral discrimination by 19F NMR.
7
concentration: In another set of experiment,
7
(1 eq, 4 eq, and
7
8
9
V. Kumar, C. E. Olsen, S. J. Schäffer, V. S. Parmar and S. V.
Malhotra, Org.Lett., 2007,
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Russo, Green Chem., 2007, , 337-341; (b) P. G. Plaza, B. A.
9, 3905-3908.
9
Bhongade and G. Singh, Synlett, 2008, 2008, 2973-2976; (c)
S. T. Handy, M. Okello and G. Dickenson, Org.Letters, 2003,
5, 2513-2515; (d) V. Kumar, C. Pei, C. E. Olsen, S. J. Schäffer,
V. S. Parmar and S. V. Malhotra, Tetrahedron: Asymmetry,
2008, 19, 664-671; (e) M. Quadir and E. Mathonneau US
11/656, 344, January 22, 2007; (f) M. A. Pereira, Mini-Rev.
Org. Chem., 2012,
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Synth., 2012, , 53-64; (h) O. N. Van Buu, A. Aupoix, N. D. T.
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9, 243-260; (g) T.-K.-T. Truong, O. Nguyen
9
10 R. Jayachandra and S. R. Reddy, Trends Carbo. Res.,2015, 7,
60-67.
11 R. Jayachandra, R. Lakshmipathy and S. R. Reddy, J. Mol. Liq.,
12 S. B. Ferreira, A. C. Sodero, M. F. Cardoso, E. S. Lima, C. R.
Kaiser, F. P. Silva Jr and V. F. Ferreira, J. Med. Chem., 2010,
53, 2364-2375.
13 S. K. Pandey, G. F. Jogdand, J. C. Oliveira, R. A. Mata, P. R.
Rajamohanan and C. V. Ramana, Chem. Eur. J., 2011, 17
12946-12954.
14 1-((3S, 4R, 5R)-5-(dimethoxymethyl)-4-
,
hydroxytetrahydrofuran-3-yl)-3-methyl-1H-imidazol-3-ium
iodide (7):To a stirred solution of compound (641 mg,
6
2.808 mmol) in dry acetonitrile (2 mL), charged methyl
iodide (598 mg/ 0.26 mL, 4.212 mmol). Stirred the reaction
mass at room temperature for 6 h. Upon completion of the
reaction, removed the solvent by vacuum distillation. The
4 | J. Name., 2012, 00, 1-3
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