40336-06-9

Basic information

• Product Name: cis-5-hydroxy-2-propylpiperidine
• CAS NO: 40336-06-9
• Molecular Weight: 143.229
• Mol File: 40336-06-9.mol

Chemical Properties

• CAS DataBase Reference: cis-5-hydroxy-2-propylpiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: cis-5-hydroxy-2-propylpiperidine(40336-06-9)
• EPA Substance Registry System: cis-5-hydroxy-2-propylpiperidine(40336-06-9)

Safety Data

• Hazardous Substances Data: 40336-06-9(Hazardous Substances Data)

Upstream product

• 92599-80-9 β-acetoxy-α-hydroxy-N-(methoxycarbonyl)-α'-propylpiperidine 
• 92599-71-8 methyl 2-propylpiperidine-1-carboxylate 
• 92599-88-7 5-Acetoxy-2-propyl-3,4-dihydro-2H-pyridine-1-carboxylic acid methyl ester 

Relevant articles and documents

Catalytic Kinetic Resolution of Disubstituted Piperidines by Enantioselective Acylation: Synthetic Utility and Mechanistic Insights

The catalytic kinetic resolution of cyclic amines with achiral N-heterocyclic carbenes and chiral hydroxamic acids has emerged as a promising method to obtain enantio-enriched amines with high selectivity factors. In this report, we describe the catalytic kinetic resolution of disubstituted piperdines with practical selectivity factors (s, up to 52) in which we uncovered an unexpected and pronounced conformational effect resulting in disparate reactivity and selectivity between the cis- and trans-substituted piperidine isomers. Detailed experimental and computational studies of the kinetic resolution of various disubstituted piperidines revealed a strong preference for the acylation of conformers in which the α-substituent occupies the axial position. This work provides further experimental and computational support for the concerted 7-member transition state model for acyl transfer reagents and expands the scope and functional group tolerance of the secondary amine kinetic resolution.

A novel route to 6-substituted piperidin-3-ols via domino cyclization of 2-hydroxy-6-phosphinyl-5-hexenyl tosylates with primary amines: Synthesis of (±)-pseudoconhydrine and (±)- epi -pseudoconhydrine

2-Hydroxy-6-phosphinyl-5-hexenyl tosylates, oxirane ring-opening products derived from glycidyl tosylates and phosphinyl-substituted allyl anions, undergo domino SN2-Michael reactions with primary amines to give 6-phosphinylmethylpiperidin-3-ols. The phosphinyl unit can be used in Horner olefination reactions. This approach is applied to the synthesis of racemic pseudoconhydrine and its epimer. Georg Thieme Verlag Stuttgart New York.

A Novel Route to 6-Substituted Piperidin-3-ols via Domino Cyclization of 2-Hydroxy-6-phosphinyl-5-hexenyl Tosylates with Primary Amines: Synthesis of (±)-Pseudoconhydrine and (±)- epi -Pseudoconhydrine

2-Hydroxy-6-phosphinyl-5-hexenyl tosylates, oxirane ring-opening products derived from glycidyl tosylates and phosphinyl-substituted allyl anions, undergo domino SN2-Michael reactions with primary amines to give 6-phosphinylmethylpiperidin-3-ols. The phosphinyl unit can be used in Horner olefination reactions. This approach is applied to the synthesis of racemic pseudoconhydrine and its epimer.

ACETOXYLATION OF PIPERIDINE DERIVATIVES AT THE 3-POSITION. STEREOSELECTIVE SYNTHESIS OF PSEUDOCONHYDRINE AND N-METHYLPSEUDOCONHYDRINE

Anodic oxidation of N-methoxycarbonylpipridine derivatives in AcOH gave 2,3-diacetoxylated products, which were shown to be useful intermediates for the stereoselective synthesis of 3-hydroxypiperidine derivatives including pseudoconhydrine and N-methylpseudoconhydrine, the Conium alcaloids.