3
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J. Paz et al.
LETTER
Garmon, S. A.; Crega, K. C.; Hendges, S. K.; Toops, D. S.;
Ford, C. W.; Zurenko, G. E. J. Med. Chem. 1996, 39, 673.
(16) García-Egido, E.; Fernández-Suárez, M.; Muñoz, L. J. Org.
Chem. 2008, 73, 2909.
(
c) Park, C.-H.; Brittelli, D. R.; Wang, C. L.-J.; Marsh, F. D.;
(17) Purchased from Aldrich chemical company.
(18) Representative Procedure for the Synthesis of 2-
Oxazolidinones 4a–j
Gregory, W. A.; Wuonola, M. A.; McRipley, R. J.; Eberly,
V. S.; Slee, A. M.; Forbes, M. J. Med. Chem. 1992, 35, 1156.
(
3) Jones, T. K.; Reamer, R. A.; Desmond, R.; Mills, S. G.
A solution of (1S,2R)-norephedrine (3a, 210 mg, 1.39 mmol)
and tetramethylphenylguanidine (290 mg, 1.52 mmol, 110
mol%) in anhyd MeCN (10 mL) was cooled to –40 °C with
a dry ice–acetone bath. Carbon dioxide was slowly bubbled
through the solution for 5 min, and then diphenylphosphoryl
azide (DPPA) (0.30 mL, 1.39 mmol, 100 mol%) was added
dropwise. Carbon dioxide bubbling was maintained for a
further 15 min, and the reaction mixture was stirred
overnight while it was slowly allowed to reach 20 °C. The
resulting solution was concentrated almost to dryness. The
J. Am. Chem. Soc. 1990, 112, 2998.
4) Wouters, J. Curr. Med. Chem. 1998, 5, 137.
5) Sibi, M. P.; Renhowe, P. A. Tetrahedron Lett. 1990, 35,
(
(
7407.
(
6) (a) Pridgen, L. N.; Prol, J. Jr.; Alexander, B.; Gillyard, L.
J. Org. Chem. 1989, 54, 3231. (b) Tamura, O.; Hashimoto,
M.; Kobayashi, Y.; Katoh, T.; Nakatani, K.; Kamada, M.;
Hayakawa, I.; Akiba, T.; Terashima, S. Tetrahedron Lett.
1992, 33, 3487.
(
7) (a) Sicker, D. Synthesis 1989, 875. (b) Gibson, C. L.;
Gillon, K.; Cook, S. Tetrahedron Lett. 1998, 39, 6733.
8) Close, W. J. J. Am. Chem. Soc. 1951, 73, 95.
residue was dissolved in CHCl (30 mL) and washed with a
3
10% Na CO (previously saturated with NaCl) solution (1×).
2
3
(
(
The aqueous layer was extracted with CHCl . The combined
3
9) (a) Ishimaru, T. Nippon Kagaku Zasshi 1960, 81, 1589.
organic layers were washed with 1 M HCl (previously
(
b) Ishimaru, T. Nippon Kagaku Zasshi 1960, 81, 1428.
saturated with NaCl) solution (1×). The aqueous layer was
(
10) Fu, Y.; Baba, T.; Ono, Y. J. Catal. 2001, 197, 91.
further extracted with CHCl . The combined organic layers
3
(
11) (a) Peng, L.; Yuan, X.; Wang, S.; Lu, S. Tetrahedron 2007,
were dried over Na SO and solvents removed under
2
4
6
3, 12419. (b) Liu, J. M.; Peng, X. G.; Liu, J. H.; Zheng,
S. Z.; Sun, W.; Xia, C. G. Tetrahedron Lett. 2007, 48, 929.
c) Wilson, T. J. Org. Chem. 1986, 51, 2977. (d) Imada, Y.;
reduced pressure. The residue was purified by flash
chromatography on SiO (hexanes–EtOAc, 4:1 to 2:1) to
2
(
afford 185 mg of (4R,5S)-4-methyl-5-phenyloxazolidin-2-
1
Mitsui, Y.; Ike, K.; Washizuka, K.; Murahashi, S. Bull.
one (4a, 75% yield) as a white solid. H NMR (400 MHz,
Chem. Soc. Jpn. 1996, 69, 2079. (e) Li, F.; Xia, C. J. Catal.
CDCl ): d = 7.45–7.27 (m, 5 H), 7.05 (s, 1 H), 5.72 (d,
3
2
004, 227, 542. (f) Chiarotto, I.; Feroci, M. Tetrahedron
J = 8.1 Hz, 1 H), 4.25 (m, 1 H), 0.83 (d, J = 6.6 Hz, 3 H)
1
3
Lett. 2001, 42, 3451. (g) Gabriele, B.; Brindisi, D.; Salerno,
G.; Costa, M.; Chiusoli, G. P. Org. Lett. 2000, 2, 625.
ppm. C NMR (100 MHz, CDCl ): d = 159.8, 134.8, 128.2,
3
128.1, 125.7, 80.8, 52.2, 17.2 ppm. IR (NaCl): n = 3240,
2980, 1756 cm . MS (EI ): m/z (%) = 239 (5) [M ], 107
(100), 104 (23). [a]D +162 (c 0.50, CHCl3).
(R)-Ethyl 2-Oxothiazolidine-4-carboxylate (4h): H NMR
–
1
+
+
(
h) Gabriele, B.; Mancuso, R.; Salerno, G.; Costa, M. J. Org.
2
7
Chem. 2003, 68, 601. (i) Miller, A. W.; Nguyen, S. T. Org.
Lett. 2004, 6, 2301. (j) Zheng, S.; Li, F.; Liu, J.; Xia, C.
Tetrahedron Lett. 2007, 48, 5883.
1
(400 MHz, CDCl ): d = 7.06 (br s, 1 H), 4.39 (ddd, J = 8.4,
3
(
12) (a) Dinsmore, C. J.; Mercer, S. P. Org. Lett. 2004, 6, 2885.
4.8, 1.0 Hz, 1 H), 4.18 (q, J = 7.1 Hz, 2 H), 3.64 (dd,
(
b) Bhanage, B. M.; Fujita, S.; Ikushima, Y.; Arai, M. Green
Chem. 2003, 5, 340. (c) Tominaga, K.-I.; Sasaki, Y. Synlett
002, 307.
J = 11.4, 8.4 Hz, 1 H), 3.51 (dd, J = 11.4, 4.8 Hz, 1 H), 1.23
1
3
(t, J = 3 × 7.1 Hz, 3 H) ppm. C NMR (100 MHz, CDCl ):
3
2
d = 174.8, 170.0, 62.0, 55.9, 31.6, 13.8 ppm. IR (NaCl): n =
–
1
+
(
(
(
13) McGhee, W.; Riley, D.; Christ, K.; Pan, Y.; Parnas, B.
3263, 2983, 1741 cm . MS (EI ): m/z (%) = 175 (22), 102
2
0
J. Org. Chem. 1995, 60, 2820.
14) Barton, D. H.; Elliot, J. D.; Géro, S. D. J. Chem. Soc., Perkin
Trans. 1 1982, 2085.
(10), 74 (60). [a]D –53 (c 3.15, CHCl3).
(19) Unpublished results.
(20) McGhee, W.; Riley, D. J. Org. Chem. 1995, 60, 6205.
15) Boyle, P. H.; Convery, M. A.; Davis, A. P.; Hosken, G. D.;
Murray, B. A. J. Chem. Soc., Chem. Commun. 1992, 239.
Synlett 2009, No. 3, 395–398 © Thieme Stuttgart · New York