91599-81-4

Basic information

• Product Name: (R)-(-)-1-Benzyl-3-hydroxypiperidine
• Synonyms: 3-PIPERIDINOL, 1-(PHENYLMETHYL)-, (3R)-;(R)-1-BENZYL-PIPERIDIN-3-OL;(R)-1-N-BENZYL-3-HYDROXY-PIPERIDINE;(R)-(-)-1-BENZYL-3-HYDROXYPIPERIDINE;(R)-1-BENZYL-3-HYDROXYPIPERIDINE;(R)-1-BENZYL-3-PIPERIDINOL;(R)-N-BENZYL-3-HYDROXYPIPERIDINE;(R)-(-)-1-BENZYL-3-HYDROXYPIPERIDINE, 97 %
• CAS NO: 91599-81-4
• Molecular Formula: C₁₂H₁₇NO
• Molecular Weight: 191.27
• Product Categories: (intermediate of benidipine)
• Mol File: 91599-81-4.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 275 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.07 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000631mmHg at 25°C
• Refractive Index: n20/D 1.547(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: (R)-(-)-1-Benzyl-3-hydroxypiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-1-Benzyl-3-hydroxypiperidine(91599-81-4)
• EPA Substance Registry System: (R)-(-)-1-Benzyl-3-hydroxypiperidine(91599-81-4)

Safety Data

• Hazard Codes: T
• Statements: 25-36/37/38
• Safety Statements: 26-45
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 91599-81-4(Hazardous Substances Data)

Usage

Description

(R)-(-)-1-Benzyl-3-hydroxypiperidine, also known as (R)-1-Benzyl-3-piperidinol, is a chiral benzylpiperidine derivative with significant biological activity. It is characterized by its unique stereochemistry, which is crucial for its pharmacological properties. (R)-(-)-1-Benzyl-3-hydroxypiperidine possesses hypotensive effects and is valuable in the development of pharmaceuticals and in vivo probes.

Uses

Used in Pharmaceutical Industry:
(R)-(-)-1-Benzyl-3-hydroxypiperidine is used as an active pharmaceutical ingredient for the development of hypotensive drugs. Its hypotensive effects make it a promising candidate for the treatment of high blood pressure and related cardiovascular conditions.
Used in Research and Development:
(R)-(-)-1-Benzyl-3-hydroxypiperidine is used in the preparation of in vivo probes for measuring endogenous acetylcholine levels. This application is vital for understanding the role of acetylcholine in various physiological processes and for the development of drugs targeting the cholinergic system.

InChI:InChI=1/C12H17NO/c14-12-7-4-8-13(10-12)9-11-5-2-1-3-6-11/h1-3,5-6,12,14H,4,7-10H2/t12-/m1/s1

Upstream product

• 62414-68-0 (3R)-piperidin-3-ol 
• 100-44-7 benzyl chloride 
• 53912-80-4 (S)-N-benzylprolinol 
• 174621-91-1 rac-N-benzyl-3-piperidinyl acetate 
• 100-39-0 benzyl bromide 
• 198976-43-1 (R)-piperidin-3-ol hydrochloride 
• 6859-99-0 3-hydroxypiperazine 
• 14813-01-5 1-benzyl-3-hydroxypiperidine 
• 1200404-98-3 rac-N-benzyl-3-piperidinyl butanoate 
• 108-22-5 Isopropenyl acetate 
• 40114-49-6 1-benzyl-3-piperidone 

Downstream Products

• 119065-61-1 (S,R)-Benidipine 
• 105979-17-7 benidipine 
• 315191-13-0 (R)-1-benzylpiperidin-3-yl 2-hydroxy-2,2-diphenylacetate 
• 873221-82-0 (R)-1-benzyl-3-fluoro-piperidine 
• 787564-48-1 (S)-N-benzyl-2-fluoromethylpyrrolidine 
• 1073136-62-5 4-{[(3R)-1-benzylpiperidin-3-yl]oxy}-6-(2-fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidine 
• 1073136-56-7 4-{[(3R)-1-benzylpiperidin-3-yl]oxy}-5-(4-ethylphenyl)-6-iodofuro[2,3-d]pyrimidine 
• 143900-43-0 tert-butyl (3R)-3-hydroxypiperidine-1-carboxylate 
• 143900-44-1 tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate 
• 404577-34-0 (R)-3-methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl ester 
• 85275-46-3 tert-butyl (3R)-3-(p-tolylsulfonyloxy)piperidine-1-carboxylate 
• 940890-90-4 (S)-3-methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl ester 
• 91599-79-0 (S)-1-N-benzyl-3-hydroxypiperidine 

Relevant articles and documents

Preparation method of piperidine alcohol compound

Discloses a preparation method of a piperidinol compound, wherein the piperidinol is selected from (R)-1 - benzyl -3 - piperidinol. 1 -benzyl -3 - piperidone as reaction raw material and application thereof LiAlH4 A chiral reagent formed by the

Chiral-1-tert-butoxy-carbonyl-3-hydroxy-piperidine, and the preparation of chiral turning method

The invention relates to preparation of chirality-1-t-butyloxycarboryl-3-hydroxy piperidine and a method for chirality turning. The preparation mainly comprises the following steps: resolving N-benzyl-3-hydroxy piperidine as a raw material to obtain a (S) or (R)-1-benzyl-3-hydroxy piperidine camphorsulfonic acid salt, performing alkali freedom to obtain (S) or (R)-1-benzyl-3-hydroxy piperidine, performing palladium carbon hydrogenation debenzylation/t-butyloxycarboryl protection to obtain (S) or (R)-1-t-butyloxycarboryl-3-hydroxy piperidine, acylating substituting sulfonyl chloride of (R) or (S)-1-substituting-3-hydroxy piperidine as a raw material to obtain (R) or (S)-1-substituting-3-hydroxy piperidine sulfonate, substituting by using substituting carboxylate to obtain (S) or (R)-1-substituting-3-hydroxy piperidine carboxylic ester, and performing alkaline hydrolysis to obtain (S) or (R)-1-substituting-3-hydroxy piperidine. The synthesis route is gentle in reaction condition, and is applicable to industrial large-scale production.

Preparation of enantiomerically pure N-heterocyclic amino alcohols by enzymatic kinetic resolution

Abstract The synthesis of both enantiomers of N-benzyl-3-hydroxypyrrolidine and N-benzyl-3-hydroxypiperidine via enzymatic kinetic resolution of the corresponding racemic esters is described. Various commercially available hydrolases were studied as biocatalysts in native and immobilized form. The best results were obtained with lipases PS, AK, CAL-B and with protease Alcalase, which were active and selective for the kinetic resolutions of racemic esters (E > 100). Under optimized reaction conditions, highly enantiomerically enriched (up to 99.5% ee) resolution products were obtained. Lipase and protease showed opposite enantiopreference on the esters, allowing the preparation of both enantiomers of the target compounds. Semi-continuous reactions in column reactors with immobilized biocatalysts were also performed with high enantioselectivities. Inversion of the configuration at C(3) of N-benzyl-3-hydroxypyrrolidine was quantitatively effected in a short number of steps.