e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Tetrahedron letters

CAN-mediated rearrangement of 4-benzhydrylidenepiperidines

MY Chang, TC Wu, CY Lin, CY Hung

Index: Chang, Meng-Yang; Wu, Tsun-Cheng; Lin, Chun-Yu; Hung, Ching-Yi Tetrahedron Letters, 2006 , vol. 47, # 47 p. 8347 - 8350

Full Text: HTML

Citation Number: 12

Abstract

Several 1-substituted phenyl-(4-phenylpiperidin-4-yl) methanones are synthesized in modest overall yields starting from the reaction of different 1-substituted 4- benzhydrylidenepiperidines via CAN-mediated rearrangement. This facile strategy was also used to synthesize meperidine analog.

benzyl 4-benzoylpiperidine-1-carboxylate Structure

benzyl 4-benzoy...

~%

4-phenyl-1-phenylmethoxycarbonylpiperidine-4-carboxylic acid Structure

4-phenyl-1-phen...

benzyl 4-benzhydrylidenepiperidine-1-carboxylate Structure

benzyl 4-benzhy...

~%

4-phenyl-1-phenylmethoxycarbonylpiperidine-4-carboxylic acid Structure

4-phenyl-1-phen...

4-(HYDROXY-DIPHENYL-METHYL)-PIPERIDINE-1-CARBOXYLIC ACID BENZYL ESTER Structure

4-(HYDROXY-DIPH...

~%

4-phenyl-1-phenylmethoxycarbonylpiperidine-4-carboxylic acid Structure

4-phenyl-1-phen...

Phenyl-piperidin-4-yl-methanone Structure

Phenyl-piperidi...

~%

4-phenyl-1-phenylmethoxycarbonylpiperidine-4-carboxylic acid Structure

4-phenyl-1-phen...

Benzyl chloroformate Structure

Benzyl chloroformate

~%

4-phenyl-1-phenylmethoxycarbonylpiperidine-4-carboxylic acid Structure

4-phenyl-1-phen...

Phenyl-piperidin-4-yl-methanone Structure

Phenyl-piperidi...

chlorophenylsulfone Structure

chlorophenylsulfone

~%

[1-(benzenesulfonyl)piperidin-4-yl]-phenylmethanone Structure

[1-(benzenesulf...

1-Piperidinecarboxylic acid, 4-benzoyl-4-phenyl-, phenylmethyl ester Structure

1-Piperidinecar...

~57%

4-phenyl-1-phenylmethoxycarbonylpiperidine-4-carboxylic acid Structure

4-phenyl-1-phen...

Phenyl-piperidin-4-yl-methanone Structure

Phenyl-piperidi...

Benzoyl chloride Structure

Benzoyl chloride

~%

PIPERIDINE-1,4-DIYLBIS(PHENYLMETHANONE) Structure

PIPERIDINE-1,4-...

Phenyl-piperidin-4-yl-methanone Structure

Phenyl-piperidi...

Tosyl chloride Structure

~%

[1-(4-methylphenyl)sulfonylpiperidin-4-yl]-phenylmethanone Structure

[1-(4-methylphe...

Phenyl-piperidin-4-yl-methanone Structure

Phenyl-piperidi...

Benzyl chloroformate Structure

Benzyl chloroformate

~%

benzyl 4-benzoylpiperidine-1-carboxylate Structure

benzyl 4-benzoy...

4-benzhydrylidene-1-(4-methylphenyl)sulfonylpiperidine Structure

4-benzhydrylide...

~59%

4-benzoyl-4-phenyl-1-(p-tolylsulphonyl)piperidine Structure

4-benzoyl-4-phe...

[1-(4-methylphenyl)sulfonylpiperidin-4-yl]-phenylmethanone Structure

[1-(4-methylphe...

~%

4-benzoyl-4-phenyl-1-(p-tolylsulphonyl)piperidine Structure

4-benzoyl-4-phe...

N/A Structure

~%

4-benzoyl-4-phenyl-1-(p-tolylsulphonyl)piperidine Structure

4-benzoyl-4-phe...

Phenyl-piperidin-4-yl-methanone Structure

Phenyl-piperidi...

~%

4-benzoyl-4-phenyl-1-(p-tolylsulphonyl)piperidine Structure

4-benzoyl-4-phe...

Tosyl chloride Structure

~%

4-benzoyl-4-phenyl-1-(p-tolylsulphonyl)piperidine Structure

4-benzoyl-4-phe...

Phenyl-piperidin-4-yl-methanone Structure

Phenyl-piperidi...

~%

4-(HYDROXY-DIPHENYL-METHYL)-PIPERIDINE-1-CARBOXYLIC ACID BENZYL ESTER Structure

4-(HYDROXY-DIPH...

Benzyl chloroformate Structure

Benzyl chloroformate

~%

4-(HYDROXY-DIPHENYL-METHYL)-PIPERIDINE-1-CARBOXYLIC ACID BENZYL ESTER Structure

4-(HYDROXY-DIPH...

Phenyl-piperidin-4-yl-methanone Structure

Phenyl-piperidi...

Methanesulfonyl chloride Structure

Methanesulfonyl...

~%

(1-methylsulfonylpiperidin-4-yl)-phenylmethanone Structure

(1-methylsulfon...

4-phenyl-1-phenylmethoxycarbonylpiperidine-4-carboxylic acid Structure

4-phenyl-1-phen...

~77%

4-PHENYL-4-PIPERIDINE CARBOXYLIC ACID Structure

4-PHENYL-4-PIPE...