5457-27-2

Basic information

• Product Name: (3R,6R)-6-propylpiperidin-3-ol
• Synonyms: (3R-trans)-6-Propyl-3-piperidinol
• CAS NO: 5457-27-2
• Molecular Formula: C₈H₁₇NO
• Molecular Weight: 143.2267
• Mol File: 5457-27-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 236°C at 760 mmHg
• Flash Point: 90.7°C
• Density: 0.932g/cm³
• Vapor Pressure: 0.00879mmHg at 25°C
• Refractive Index: 1.458
• CAS DataBase Reference: (3R,6R)-6-propylpiperidin-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,6R)-6-propylpiperidin-3-ol(5457-27-2)
• EPA Substance Registry System: (3R,6R)-6-propylpiperidin-3-ol(5457-27-2)

Safety Data

• Hazardous Substances Data: 5457-27-2(Hazardous Substances Data)

Usage

Description

(3R,6R)-6-propylpiperidin-3-ol is a chiral organic compound with the molecular formula C10H21NO. It belongs to the class of piperidines, which are cyclic amines containing a six-membered heterocyclic ring derived from piperidine. The (3R,6R) prefix indicates the stereochemical configuration of the molecule, which is crucial for its pharmacological activity. (3R,6R)-6-propylpiperidin-3-ol is commonly used in the synthesis of pharmaceuticals and research chemicals and may have potential applications in the development of new drugs and therapeutic agents.

Uses

Used in Pharmaceutical Synthesis:
(3R,6R)-6-propylpiperidin-3-ol is used as a key intermediate in the synthesis of various pharmaceuticals and research chemicals. Its unique stereochemistry allows for the development of enantiomerically pure compounds, which can exhibit different biological activities and reduce potential side effects.
Used in Drug Development:
(3R,6R)-6-propylpiperidin-3-ol is used as a building block in the development of new drugs and therapeutic agents. Its chiral nature and versatile chemical properties make it a valuable component in the design and synthesis of novel pharmaceuticals with improved efficacy and selectivity.
Used in Organic Chemistry Research:
(3R,6R)-6-propylpiperidin-3-ol is used as a model compound in organic chemistry research to study the effects of stereochemistry on chemical reactivity and biological activity. This knowledge can be applied to the design of more effective and selective drugs and to understand the fundamental principles of stereoselective synthesis.

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 
• 4808-69-9 6-methyl-3-sulfonylpyridine 
• 217302-90-4 5-nitro-2-propylpyridine 
• 4548-45-2 2-chloro-5-nitropyridine 
• 228862-38-2 5-methoxy-2-propylpyridine 
• 55270-47-8 5-methoxy-2-picoline 
• 1121-78-4 5-Hydroxy-2-methylpyridine 
• 90376-92-4 6-propyl-2,3-pyridinedicarboxylic acid 
• 856858-01-0 (6-propyl-[3]pyridyl)-carbamic acid ethyl ester 
• 118419-90-2 Ethyl 6-propylnicotinate 
• 847046-96-2 6-propylnicotinic acid 
• 217302-91-5 5-amino-2-propylpyridine 

Downstream Products

• 155511-85-6 (2S,5S)-(+)-1-(benzyloxycarbonyl)-5-hydroxy-2-propylpyperidine 

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.

Hydroboration of Enecarbamates and the Synthesis of β-Hydroxypiperidine Alkaloids

The β-hydroxypiperidine alkaloids 5, 6 and 8 were diastereoselectively synthesized using hydroboration of enecarbamates 2b-c as a key step.