S. Pattanayak, S. Sinha / Tetrahedron Letters 52 (2011) 34–37
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12. (a) Radzki, S.; Giannotti, C. J. Chem. Soc., Dalton Trans. 1993, 676; (b) Yunlu, K.;
Gradeff, P. S.; Edelstein, N.; Kot, W.; Shalimoff, G.; Streib, W. E.; Vaartstra, B. A.;
Caulton, K. G. Inorg. Chem. 1991, 30, 2317.
13. Gerson, F.; Huber, W. Electron Spin Resonance Spectroscopy of Organic Radicals;
Wiely-VCH, 2003.
Supplementary data
Supplementary data associated with this article can be found, in
14. General procedure: The substrate (1 equiv) was added to a solution of CAN
(20 mol %) in minimum amount of water (roughly 15 equiv). The reaction
mixture was dissolved in dichloromethane and stirred magnetically. Acetic
acid (10 equiv) was added to the solution and left to stir at rt for the required
time mentioned in Table 2. Upon completion of the reaction, the solvent was
evaporated under reduced pressure and worked up in the following methods.
Method A: The solid residue was washed twice with petroleum ether to
remove the by product trityl alcohol. The residue was then dissolved in
methanol and filtered through a short pad of celite. Removal of the solvent
under reduced pressure yielded the free amine. Method B: Water and acetic
acid were removed from the reaction mixture in vacuo. The residue was
dissolved in dry dichloromethane, followed by the addition of triethylamine
(2.5 equiv) and acetic anhydride or benzoyl chloride (1.5 equiv). After the
completion of the reaction, the solvent was evaporated. The residue was
extracted with ethyl acetate twice. The combined organic layer was washed
with water and brine and finally dried (Na2SO4). Solvent was removed under
reduced pressure and the residue obtained was purified by silica gel column
chromatography to afford the acylated amine.
References and notes
1. Greene, T. W.; Wuts, P. G. M. Greene’s Protective Groups in Organic Synthesis, 4th
ed.; John Wiley & Sons: New York, 2007.
2. MacCoss, M.; Cameron, D. J. Carbohydr. Res. 1978, 60, 206. and references cited
therein.
3. (a) Lu, R. J.; Liu, D.; Giese, R. W. Tetrahedron Lett. 2000, 41, 2817; (b) Köster, H.;
Sinha, N. D. Tetrahedron Lett. 1982, 23, 2641.
4. N-Detritylation: (a) Applegate, H. E.; Cimarusti, C. M.; Donfini, J. E.; Funke, P.
T.; Koster, W. H.; Puar, M. S.; Slusarchyk, W. A.; Young, M. G. J. Org. Chem.
1979, 44, 811; (b) Bejjani, J.; Chemla, F.; Audouin, M. J. Org. Chem. 2003, 68,
9747; (c) Ishii, K.; Sone, T.; Shimada, Y.; Shigeyama, T.; Noji, M.; Sugiyama,
S. Tetrahedron 2004, 60, 10887; (d) Baraniak, J.; Kaczmarek, R.; Wasilewska,
E.; Korczyn´ ski, D.; Stec, W. J. Tetrahedron Lett. 2004, 45, 4269; (e) Shintani,
R.; Duan, W.-L.; Nagano, T.; Okada, A.; Hayashi, T. Angew. Chem., Int. Ed.
2005, 44, 4611.
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S. K.; Songster, M. F.; Colpitts, T. L.; Hegyes, P.; Barany, G.; Castellino, F. J. J. Org.
Chem. 1993, 58, 4993.
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Synthesis 2004, 8, 1274; (c) Nesvadba, H.; Roth, H. Monatsh. Chem. 1967, 98,
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15. Selected spectral data:
Compound 8: white solid; 1H NMR (300 MHz, CDCl3): d 0.86 (d, 3H, J = 7.0 Hz),
2.05 (br s, 1H), 3.10 (d, 2H, J = 5.7 Hz), 3.26 (q, 1H, J = 7.0 Hz), 3.72 (s, 3H), 4.56
(m, 1H), 7.19–7.22 (m, 2H), 7.25–7.36 (m, 18H), 7.68 (m, 1H); 13C NMR
(75 MHz, CDCl3): 21.2, 29.7, 38.0, 52.2, 52.7, 53.9, 72.0, 77.2, 126.2, 126.4,
127.1, 127.6, 128.0, 128.2, 128.4, 128.5, 128.8, 128.9, 129.4, 136.0, 145.5, 171.7,
175.4; HRMS calcd for C32H32N2O3Na (M+Na)+ 515.2311, found 515.2316.
Compound 9: white solid; 1H NMR (300 MHz, CDCl3): d 0.89–1.06 (m, 2H), 1.47–
1.63 (m, 2H), 2.85 (dt, 1H, J = 11.0, 6.8 Hz), 3.38–3.46 (m, 1H), 3.49 (s, 3H), 3.90
(dd, 1H, J = 7.8, 1.8 Hz), 7.16 (t, 3H, J = 7.2 Hz), 7.23–7.32 (m, 6H), 7.57 (d, 6H,
J = 7.8 Hz); 13C NMR (75 MHz, CDCl3): 24.4, 31.4, 50.1, 51.7, 62.9, 126.3, 127.8,
129.4, 144.9, 177.4; HRMS calcd for C25H25NO2Na (M+Na)+ 394.1783, found
394.1782.
7. (a) Hwu, J. R.; Jain, M. L.; Tsay, S. C.; Hakimelahi, G. H. Chem. Commun. 1996,
545; (b) Hwu, J. R.; Jain, M. L.; Tsai, F.-Y.; Tsay, S.-C.; Balakumar, A.; Hakimelahi,
G. H. J. Org. Chem. 2000, 65, 5077.
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11. Surendra, K.; Krishnaveni, N. S.; Rama Rao, K. Tetrahedron Lett. 2005, 46, 4111.