5457-27-2

Usage

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

• 20609-24-9 6-propyl-pyridin-3-ol 
• 1796-27-6 piperidine-1-carboxylic acid methyl ester 
• 4808-69-9 6-methyl-3-sulfonylpyridine 
• 56475-86-6 2-methoxy-piperidine-1-carboxylic acid methyl ester 
• 92599-80-9 β-acetoxy-α-hydroxy-N-(methoxycarbonyl)-α'-propylpiperidine 
• 87830-36-2 2-exo-Propyl-1-azabicyclo<3.1.0>hexane 
• 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 
• 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 

Downstream Products

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

Relevant academic research and scientific papers

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.

Synthesis of β-hydroxypiperidine alkaloids by anodic oxidation of carbamates and hydroboration

The β-hydroxypiperidine alkaloids (±)-pseudoconhydrine, (±)-N-methylpseudoconhydrine, (-)-5-hydroxysedamine, and (+)-sedacryptine were synthesized. Successive functionalization of the piperidine ring via anodic methoxylation allowed the regio- and stereos

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.

Applications of Intramolecular Amidomercuration. 2. Synthesis of trans-5-Hydroxy-2-propylpiperidine, (+/-)-Pseudoconhydrine

A method for the stereoselective conversion of δ-alkenyl carbamates into trans-2-alkyl-5-substitutes-piperidines utilizing intramolecular amidomercuration as key step has been developed.As a specific illustration of the method, a synthesis of one of the Hemlock alkaloids, (+/-)-Pseudoconhydrine (trans-5-hydroxy-2-propylpiperidine, 1) was completed.The organomercurial 7a obtained from the intramolecular amidomercuration of 4--7-octene (6) was converted to the corresponding trans-5-(iodomethyl)-2-propylpyrrolidine derivative 7b.Cleavage of the carbamate and treatment with base generated the bicyclic aziridine 2-exo-propyl-1-azabicyclohexane (8a).Treatment of this aziridine with excess trifluoroacetic acid gave ring opening to the disubstituted pyrrolidine derivative 9a exclusively.Ring opening of the analogous aziridine 8b with HCl gave mixtures of pyrrolidine 9b and piperidine 10b.However, these derivatives can be equilibrated through the neutral amine to a mixture consisting of ca. 85percent of the piperidine derivate.Slow addition of trifluoroacetic acid to the aziridine 8a allowed for equilibration to the piperidine 14 as the major product.Hydrolysis and purification gave pure racemic pseudoconhydrine.This sequence illustrates a synthetic equivalent to anti-Markovnikov cyclofunctionalization of δ-alkenyl carbamates.In addition, this study provided new information on the regiochemistry of ring opening bicyclic aziridines.

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.