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CN
  • A new synthesis of 2,3-di- or 2,3,3-trisubstituted 2,3-dihydro-4-pyridones by reaction of 3-ethoxycyclobutanones and N-p-toluenesulfonyl imines using titanium(IV) chloride: synthesis of (+/-)-bremazocine.

A new synthesis of 2,3-di- or 2,3,3-trisubstituted 2,3-dihydro-4-pyridones by reaction of 3-ethoxycyclobutanones and N-p-toluenesulfonyl imines using titanium(IV) chloride: synthesis of (+/-)-bremazocine.

Organic letters (2010-06-24)
Jun-ichi Matsuo, Ryohei Okado, Hiroyuki Ishibashi
ABSTRACT

N-p-Toluenesulfonyl (Ts) aldimines reacted with 3-ethoxycyclobutanones by catalysis of titanium(IV) chloride to afford 2,3-di- or 2,3,3-trisubstituted N-Ts-2,3-dihydro-4-pyridones. Synthesis of (+/-)-bremazocine was efficiently accomplished by using this method.

MATERIALS
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Product Description

Sigma-Aldrich
Titanium(III) chloride solution, 10-15% TiCl3 basis