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Organic & Biomolecular Chemistry
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ARTICLE
19 A. R. Howell, and G. Pattenden, J. Chem. Soc., Chem. Commun.
potassium peroxodisulfate (54 mg, 200 µmol, 1.0 equiv.) was
evacuated and purged with argon and 1,2-dichloroethane
(1.50 mL) and water (0.50 mL) were added. The biphasic
mixture was stirred at 80 °C under an argon atmosphere for
20 h. Then, the reaction mixture was diluted water (5.0 mL) and
extracted with EtOAc (3x 10.0 mL). The combined organic
phases were washed with brine (10.0 mL), dried over MgSO4,
filtered and concentrated under reduced pressure. The product
was purified by flash column chromatography (petroleum
ether:EtOAc= 50:1). The alkoxyamine 12b was collected as a
pale-yellow oil (41 mg, 166 µmol, 83%). Rf = 0.50 (petroleum
1990, 103.
DOI: 10.1039/D0OB01773F
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1
ether:EtOAc 50:1); H-NMR (CDCl3, 600 MHz): δ [ppm] 7.38 -
7.28 (m, 5H, ArH), 4.83 (s, 2H, CH2ON), 1.64 - 1.34 (m, 6H,
3×CH2), 1.26 (s, 6H, 2×CH3), 1.16 (s, 6H, 2×CH3); 13C-NMR (CDCl3,
150 MHz): δ [ppm] 138.5 (q, ArC), 128.4 (t, 2×ArC), 127.6 (t,
2×ArC), 127.4 (t, ArC), 78.9 (s, CH2ON), 60.2 (q, 2×C(CH3)2), 39.9
(s, 2×CH2), 33.2 (p, 2×CH3), 20.4 (p, 2×CH3), 17.3 (s, CH2(CH2)2).
The analytical data are consistent with those reported in the
literature.35
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Graphical abstract
The oxidative radical decarboxylation of carboxylic acids with
TEMPO as radical scavenger in a biphasic solvent system is
reported which is successfully used in a new synthetic approach
for the antidepressants Indatraline.
2-
S2O8
O
aqueous phase
O
N
O
-
SO4
2-
R
+ SO4
CH2
R
K2CO3
TEMPO
O
Cl
Cl
N
O
R
OH
precursor of
Indatraline
R
organic phase
17 a) A. Studer, Angew. Chem. Int. Ed. 2000, 39, 1108; b) M.
Šimek, K. Bártová, R. Pohl, I. Císařová, and U. Jahn, Angew.
Chem. Int. Ed. 2020, 59, 6160.
18 Q. Zhu, E. C. Gentry, and R. R. Knowles, Angew. Chem. Int. Ed.
2016, 55, 9969.
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