H.-C. Hsu, D.-R. Hou / Tetrahedron Letters 50 (2009) 7169–7171
7171
3
779; (c) Kren, V.; Fiserova, A.; Weignerova, L.; Sibor, I.; Halada, P.; Prikrylova,
Acknowledgments
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This research was supported by the National Science Council
(
NSC 95-2113-M-008-007-MY3), Taiwan, ROC. We are grateful to
(
g) Taggart, M. S.; Richter, G. H. J. Am. Chem. Soc. 1934, 56, 1385.
Ms. Ping-Yu Lin at the Institute of Chemistry, Academia Sinica,
and Valuable Instrument Center in National Central University
for obtaining mass analysis.
6.
(a) Evans, G. B.; Furneaux, R.; Hutchison, T. L.; Kezar, H. S.; Morris, P. E., Jr.;
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8
1
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Supplementary data
Clardy, J. J. Org. Chem. 1993, 58, 2862; (f) Dhanak, D.; Reese, C. B. J. Chem. Soc.,
Perkin Trans. 1 1986, 2181.
Experimental procedures, 1H NMR and 13C NMR spectra for all
7. (a) Figueroa-Perez, S.; Bennabi, S.; Schirok, H.; Thutewohl, M. Tetrahedron Lett.
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2
127, 5970.
8
9
.
.
Yudina, L. N.; Bergman, J. Tetrahedron 2003, 59, 1265.
Typical procedure: Lithium aluminum hydride (94.0 mg, 2.5 mmol) was added
to the solution of tert-butyl 1H-indole-1-carboxylate (100.0 mg, 0.46 mmol)
and THF (5 mL) portionwise at 0 °C. After the gas evolution ceased, the flask
was transferred to a preheated oil bath (50 °C). After being stirred at 50 °C
References and notes
for 30 min, the reaction was quenched with satd NH
mixture was extracted with ether. The organic layers were combined, dried
over Na SO4(s), filtered, and concentrated. The crude product was further
purified by column chromatography (SiO , ethyl acetate/hexanes, 1:3; R
.20) to give 1-hydroxymethyl-1H-indole (53.4 mg, 0.36 mmol, 79%) as
4
Cl(aq) and the reaction
1
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(a) Smith, M. B.; March, J. March’s Advanced Organic Chemistry; Wiley-
Interscience: New York, 2007. pp 1281–1283; (b) Chudek, J. A.; Foster, R.;
Young, D. J. Chem. Soc., Perkin Trans. 2 1985, 1285.
2
2
f
:
0
a
2
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J.-Y. J. Med. Chem. 2007, 50, 4548; (b) Kemnitzer, W.; Drewe, J.; Jiang, S.; Zhang, H.;
Crogan-Grundy, C.; Labreque, D.; Bubenick, M.; Attardo, G.; Denis, R.; Lamothe,
S.; Gourdeau, H.; Tseng, B.; Kasibhatla, S.; Cai, S. X. J. Med. Chem. 2008, 51, 417.
Deguest, G.; Bischoff, L.; Fruit, C.; Marsais, F. Org. Lett. 2007, 9, 1165.
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Bioorg. Med. Chem. Lett. 2000, 10, 1121; (b) Bundgaard, H. In Design of Prodrugs;
Bundgaard, H., Ed.; Springer: Amsterdam, 1985; pp 1–92.
1
light yellow oil. H NMR (CDCl
3
, 300 MHz) d 2.70 (br, 1H), 5.54 (s, 2H), 6.52
(
7
1
1
dd, J = 3.3 Hz, J = 0.8 Hz, 1H), 7.11–7.26 (m, 3H), 7.42–7.45 (m, 1H), 7.61–
.64 (m, 1H); 13C NMR (CDCl
22.1, 127.3, 129.1, 135.5; HRMS-EI (m/z): [M] calcd for (C
47.0684; found 147.0683. The spectroscopic data were consistent with
, 75 MHz) d 69.4, 102.7, 109.4, 120.2, 121.0,
3
+
9 9
H NO),
3
4
.
.
6f
the reported value.
1
1
0. Yatvin, M. B.; Pederson, R. L. US2003087803, 2003.
1. Evans, D. A.; Borg, G.; Scheidt, K. A. Angew. Chem., Int. Ed. 2002, 41, 3188.
5
.
(a) McFarland, J. M.; Joshi, N. S.; Francis, M. B. J. Am. Chem. Soc. 2008, 130, 7639;
(
b) Sui, Y.; Liu, L.; Zhao, J.-L.; Wang, D.; Chen, Y.-J. Tetrahedron Lett. 2007, 48,