Heteroalicyclic Aminoalkanol. I. Syntheses of DL-2-Piperidinemethanol and meso-cis-2,6-Piperidinedimethanol and Reactions of Intermediates

スポンサーリンク

概要

• 論文の詳細を見る

• Syntheses of DL-2-piperidinemethanol (XXXIII) and meso-cis-2,6-piperidinedimethanol (XXXIV) were accomplished through a few steps from 2-picoline (I) and 2,6-lutidine (II) respectively. The configuration of XXXIV was confirmed. The following reactions of synthetic intermediates were also examined. 6-Methylpicolinaldehyde (IX) was obtained by acetolysis followed by hydrolysis from 2-bromomethyl-6-methylpyridine 1-oxide (X) through α-bromo-6-methyl-2-pyridinemethanol acetate (XIV) in a yield, 16.2% and from 2-ethylthiomethyl-6-methylpyridine 1-oxide (XII) through α-ethylthio-6-methyl-2-pyridinemethanol acetate (XVII) in a yield, 84.2%. Unusually enough, alkaline treatment at room temperature converted 2-bromomethylpyridine 1-oxide (XIX) to 2,2'-oxydimethyldipyridine 1,1'-dioxide (XXVI) in a yield as high as 88.3%. The ether formation was found in the same treatment of analogues.

• 公益社団法人日本薬学会の論文
• 1965-03-25

著者

• 春日 成暉

  Faculty Of Pharmaceutical Sciences Kyushu University:(present Address) Sankyo Research Laboratories

• 田口 胤三

  Faculty of Pharmaceutical Sciences, Kyushu University

• 田口 胤三

  Faculty Of Pharmaceutical Sciences Kyushu University

関連論文

• Catalytic Rearrangement of O, S-Dialkyl Dithiocarbonates to S, S-Dialkyl Dithiocarbonates. IV. Use of Boron Trifluoride Etherate as Catalyst
• Rearrangement and trans-Elimination contrary to the Chugaev Reaction Rule. XIII. Solvent Effect on Rearrangement Reaction of Allylic Xanthates and a Correction of the Former Report
• Catalytic Rearrangement of Xanthates to Dithiolcarbonates
• Rearrangement and trans-Elimination contrary to the Chugaev Reaction Rule. IX. Thermal Rearrangement of 2-Cycloalkenyl S-Alkyl Xanthate
• Rearrangement and trans-Elimination contrary to the Chugaev Reaction Rule. VIII. Thermal Rearrangement of 2-Alkenyl S-Alkyl Xanthate
• Heteroalicyclic Aminoalkanol. II. Reactions of DL-2-Piperidinemethanol involving the Formation of DL-1-Azabicyclo[4,1,0]heptane
• Heteroalicyclic Aminoalkanol. I. Syntheses of DL-2-Piperidinemethanol and meso-cis-2,6-Piperidinedimethanol and Reactions of Intermediates
• thionamides. I. Synthesis. Demethylation of their N, N-Dimethyl Derivatives by Sulfur.
• Deamination Reaction of Diastereomeric DL-2 (1-Phenylcyclohexyl) cyclohexylamine with Nitrous Acid
• Grignard Reaction and Products. V. Reduction of Ketoximes to Aziridines with Grignard Reagents
• Grignard Reaction and Products. VI. The Reaction of Grignard Reagents with 2-Phenoxy-and 2-Benzyloxy-cyclohexanone Oximes
• Sulfinylamine Chemistry. I. A New Degradation Reaction of α-Amino Acid with N-Sulfinylaniline
• Grignard Reaction and Products. II. A Novel Intramolecular Cyclization in the Grignard Reaction of Alicyclic Ketoxime containing an Aromatic Nucleus
• Grignard Reaction and Products. I. 1,4-Addition of Arylmagnesium Bromide to 2-Alkylidenecyclohexanone and the Oxidative Cleavage therein
• Configurational Effect in N-Alkylation of Diastereomeric 2-Aminocyclohexanol.

もっと見る 閉じる

スポンサーリンク