Hydrogenolysis of the cyclopropyl group into an isopropyl group in the presence of a platinum catalyst and hydrobromic acid

Tetrahedron

Volumn 65, Issue 51, 2009, Pages 10623-10630

  Fujii, Hideaki ^a   Okada, Kayoko ^a   Ishihara, Marina ^a   Hanamura, Shinichi ^a   Osa, Yumiko ^a   Nemoto, Toru ^a   Nagase, Hiroshi ^a  

^a KITASATO UNIVERSITY   (Japan)

Author keywords

Cyclopropane ring; Hydrogenolysis; Isopropyl; Platinum catalyst

Indexed keywords

ALIPHATIC AMINE; CYCLOBUTANE; CYCLOBUTYLMETHYLAMINE; CYCLOPROPANE DERIVATIVE; CYCLOPROPYLMETHYLAMINE; HYDROBROMIC ACID; METAL OXIDE; MORPHINAN DERIVATIVE; NALTREXONE; PLATINUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; HYDROGENOLYSIS; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME;

EID: 70449512477     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.10.064     Document Type: Article

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41. 1H NMR spectra of crude product showed decrease in signals indicating cyclopropane ring, but value of integral stemmed from aromatic protons was smaller than the theoretical value. Aliphatic methoxy signal (around 3.4 ppm) and increase in value of integral derived from aliphatic protons (around 1-2 ppm) were also observed. Taken together, these observations strongly suggest that reduction of benzene ring would proceed concomitantly.