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36148931005
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and references therein
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(f) Tichenor, M. S.; MacMillan, K. S.; Stover, J. S.; Wolkenberg, S. E.; Pavani, M. G.; Zanella, L.; Zaid, A. N.; Spalluto, G.; Rayl, T. J.; Hwang, I.; Baraldi, P. G.; Boger, D. L. J. Am. Chem. Soc. 2007, 129, 14092; and references therein.
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0016607018
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N-Cyclopropyltryptamine was also described as a potent monoamine oxidase inhibitor. See: Winn, M.; Horrom, B. W.; Rasmussen, R. R.; Chappell, E. B.; Plotnikoff, N. P. J. Med. Chem. 1975, 18, 437.
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(b) N-Cyclopropyltryptamine was also described as a potent monoamine oxidase inhibitor. See: Winn, M.; Horrom, B. W.; Rasmussen, R. R.; Chappell, E. B.; Plotnikoff, N. P. J. Med. Chem. 1975, 18, 437.
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33745121849
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Tsotinis, A.; Vlachou, M.; Papahatjis, D. P.; Calogeropoulou, T.; Nikas, S. P.; Garratt, P. J.; Piccio, V.; Vonhoff, S.; Davidson, K.; Teh, M.-T.; Sugden, D. J. Med. Chem. 2006, 49, 3509.
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Sugden, D.11
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33746112621
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Raoul, M.; Patigny, D.; Fabis, F.; Dauphin, F.; Rault, S.; Sapi, J.; Laronze, J.-Y. J. Enzym. Inhib. Med. Chem. 2006, 251.
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20144366827
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(b) Holenz, J.; Mercè, R.; Diaz, J. L.; Guitart, X.; Codony, X.; Dordal, A.; Romero, G.; Torrens, A.; Mas, J.; Andaluz, B.; Hernandez, S.; Monroy, X.; Sanchez, E.; Hernandez, E.; Pérez, R.; Cubi, R.; Sanfeliu, O.; Bushchmann, H. J. Med. Chem. 2005, 48, 1781.
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Sapi, J.; Grébille, Y.; Laronze, J.-Y.; Lévy, J. Synthesis 1992, 383.
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Sapi, J.1
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22
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33748630852
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An alternative approach involving the titanium-mediated cyclopropanation of N,N-dialkylamides should be envisioned, but requires the preparation of the amides. For the reaction, see: (a) Chaplinski, V, de Meijere, A. Angew. Chem, Int. Ed. Engl. 1996, 35, 413
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An alternative approach involving the titanium-mediated cyclopropanation of N,N-dialkylamides should be envisioned, but requires the preparation of the amides. For the reaction, see: (a) Chaplinski, V.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 413.
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23
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de Meijere, A.1
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24
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0001581110
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For related applications, see: c
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For related applications, see: (c) Cao, B.; Xiao, D.; Joullié, M. M. Org. Lett. 1999, 1, 1799.
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Cao, B.1
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(g) Larquetoux, L.; Ouhamou, N.; Chiaroni, A.; Six, Y. Eur. J. Org. Chem. 2005, 4654.
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Eur. J. Org. Chem
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Larquetoux, L.1
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Six, Y.4
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30
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28444454943
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(a) Laroche, C.; Behr, J. B.; Szymoniak, J.; Bertus, P.; Plantier-Royon, R. Eur. J. Org. Chem. 2005, 5084.
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Laroche, C.1
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Plantier-Royon, R.5
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(c) Pearson, M.; Plantier-Royon, R.; Szymoniak, J.; Bertus, P.; Behr, J. B. Synthesis 2007, 3589.
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Synthesis
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Pearson, M.1
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Behr, J.B.5
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46449120890
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The ketone by-product might also be obtained by the hydrolysis of metallacycle B (Scheme 2). This assumption was ruled out by deuterolysis of the reaction media (no trace of deuterium was observed on the methyl moiety).
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The ketone by-product might also be obtained by the hydrolysis of metallacycle B (Scheme 2). This assumption was ruled out by deuterolysis of the reaction media (no trace of deuterium was observed on the methyl moiety).
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35
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0002973636
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Chaplinski, V.; Winsel, H.; Kordes, M.; de Meijere, A. Synlett 1997, 111.
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Synlett
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Chaplinski, V.1
Winsel, H.2
Kordes, M.3
de Meijere, A.4
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36
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46449104796
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General Procedure for the MeTi(Oi-Pr) 3-Mediated Cyclopropanation of Nitriles 10a-c and 11a,b (Table 1, To a solution of the nitrile (1 mmol) and MeTi(Oi-Pr)3 (1.5 mmol) in THF (10 mL) was added dropwise under argon the Grignard reagent (1.5 mmol, The yellow solution darkened gradually within 5 min. After stirring for 1.5 h, BF3-OEt2 was added (2 mmol, After 30 min, the dark mixture was quenched with 1 M HC1 (10 mL, EtOAc (20 mL) was added, followed by 3 M NaOH (10 mL, The mixture was stirred until the blue aqueous solution become white. The aqueous phase was extracted with EtOAc (2 x 20 mL, After drying (MgSO4) and evaporation of the solvents, the crude material was purified by flash chromatography EtOAc
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4) and evaporation of the solvents, the crude material was purified by flash chromatography (EtOAc).
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37
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46449128107
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2S 327.1167; found: 327.1169.
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2S 327.1167; found: 327.1169.
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38
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46449089009
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The cyclopropanation of unprotected 8 gave only a low yield of the primary cyclopropylamine.
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The cyclopropanation of unprotected 8 gave only a low yield of the primary cyclopropylamine.
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39
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0027246318
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Street, L. J.; Baker, R.; Castro, J. L.; Chambers, M. S.; Guiblin, A. R.; Hobbs, S. C.; Matassa, V. G.; Reeve, A. J.; Beer, M. S.; Middlemiss, D. N.; Noble, A. J.; Stanton, J. A.; Scholey, K.; Hargreaves, R. J. J. Med. Chem. 1993, 36, 1529.
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(1993)
J. Med. Chem
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, pp. 1529
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Street, L.J.1
Baker, R.2
Castro, J.L.3
Chambers, M.S.4
Guiblin, A.R.5
Hobbs, S.C.6
Matassa, V.G.7
Reeve, A.J.8
Beer, M.S.9
Middlemiss, D.N.10
Noble, A.J.11
Stanton, J.A.12
Scholey, K.13
Hargreaves, R.J.14
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40
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46449102278
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Selected data: N,N-Dimethyl-1, 1-benzenesulfonyl-lH-indol-3-yl)methyl]cyclopropylamine (6a, yellow oil. IR (neat, 3365, 2916, 2845, 1634, 1445, 1264, 1119 cm-1. 1H NMR (300 MHz, CDCl3, δ, 0.25-0.57 (m, 4 H, 2.45 (s, 6 H, 3.01 (s, 2 H, 7.25-7.52 (m, 7 H, 7.80-7.83 (m, 2 H, 7.98 (d, J, 8.1 Hz, 1 H, 13C NMR (75 MHz, CDCl3, δ, 13.3,21.1,40.9,43.7, 113.9, 119.6, 120.3, 123.3, 124.2, 124.7,126.5,129.1,131.7, 133.7,135.1,138.0. HRMS (El, mlz [M, calcd for C 20H22N2O2S: 354.1402; found: 354.1398. N,N-Dimethyl-1, 1-methyl-2-vinyl-1H- indol-3-yl)methyl]cyclopropylamine (7a, yellow oil. IR (neat, 3054, 2986, 2845, 1628, 1437, 1262 cm-1. 1HNMR (300 MHz, CDCl 3, δ, 0.30-0.55 (m, 4 H, 2.63 (s, 6 H, 3.30 (s, 2 H, 3.70 (s, 3 H, 5.50 dd, J
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2: 255.1861; found: 255.1855.
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