Selective C-N bond oxidation: demethylation of N-methyl group in N-arylmethyl-N-methyl-α-amino esters utilizing N-iodosuccinimide (NIS)

Tetrahedron Letters

Volumn 49, Issue 4, 2008, Pages 598-600

  Katoh, Takahiro ^a   Watanabe, Tsunefumi ^a   Nishitani, Mitsuyoshi ^a   Ozeki, Minoru ^a   Kajimoto, Tetsuya ^a   Node, Manabu ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ESTER DERIVATIVE; METHOXYAMINE; METHYL GROUP; N IODOSUCCINIMIDE; N METHYL ALPHA AMINO ESTER DERIVATIVE; SUCCINIMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; DEMETHYLATION; HYDROGENOLYSIS; OXIDATION;

EID: 37549009179     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.11.162     Document Type: Article

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41. The manuscript is now in preparation.
42. General procedure of demethylation with NIS/acetonitrile system: To an acetonitrile (1 ml) solution of 3a (40 mg, 0.14 mmol) was added NIS (64 mg, 0.28 mmol), and then the mixture was stirred at rt. After standing for 1 h, O-methylhydroxylamine hydrochloride (24 mg, 0.28 mmol) was added to the reaction mixture, which was stirred at rt for 1.5 h. The mixture was poured into a saturated aqueous solution of sodium hydrogen carbonate, which was extracted with chloroform. The combined organic layer was washed with a 5% aqueous solution of sodium thiosulfate and brine, dried over with potassium carbonate, filtered, and concentrated in vacuo. The crude residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate = 8:1 to 1:1) to give 2a (32 mg, 83%) and 4 (4 mg, 14%).
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