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

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

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 
• 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 
• 108-22-5 Isopropenyl acetate 
• 14813-01-5 1-benzyl-3-hydroxypiperidine 
• 40114-49-6 1-benzyl-3-piperidone 
• 1200404-98-3 rac-N-benzyl-3-piperidinyl butanoate 
• 53912-80-4 (S)-N-benzylprolinol 

Downstream Products

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

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

Stereo-complementary bioreduction of saturated N-heterocyclic ketones

The asymmetric bioreduction of several saturated N-heterocyclic ketones is demonstrated in a stereo-complementary fashion using the ketoreductases READH and ChKRED20 for the production of (S)- and (R)-alcohols, respectively. The reaction accepts substrates with a five-, six- or seven-membered ring, and exhibits excellent stereoselectivity when using 2-propanol as both the ultimate reducing agent and cosolvent, achieve >99% ee in the majority of cases for both enantiomers.

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.

NOVEL COMPOUNDS AS ANTI-TUBERCULAR AGENTS

The present invention relates to novel compounds of formula (1): The present invention also discloses compounds of formula (1) along with other pharmaceutical acceptable excipients and use of the compounds as anti-tubercular agents.

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.

An efficient dynamic kinetic resolution of N-heterocyclic 1,2-amino alcohols

A chemoenzymatic dynamic kinetic resolution (DKR) of N-heterocyclic amino alcohols is described. Various lipases were studied as biocatalysts for the kinetic resolution of N-heterocyclic 1,2-amino alcohols. The influence of the support of the enzymes on t

Simple one-pot process for the bioresolution of tertiary amino ester protic ionic liquids using subtilisin

An efficient hydrolase-catalyzed bioresolution of tertiary amino ester protic ionic liquids has been demonstrated. Protic ionic liquids have been prepared in one step from the corresponding tertiary amino alcohols by treatment with butyric anhydride. Afte

Stereospecific rearrangement of β-amino alcohols catalyzed by H 2SO4

Highly enantioselective rearrangement of β-amino alcohols was realized by using a catalytic amount of H2SO4. Georg Thieme Verlag Stuttgart.

Highly enantioselective synthesis of β-amino alcohols: A catalytic version

(Chemical Equation Presented) Highly enantioselective rearrangement of β-amino alcohols was realized by using a catalytic amount of trifluoroacetic anhydride.

Synthesis, 18F-labeling, and biological evaluation of piperidyl and pyrrolidyl benzilates as in vivo ligands for muscarinic acetylcholine receptors

A series of 31 compounds based on the piperidyl or pyrrolidyl benzilate scaffold were prepared from methyl benzilate and 4-piperidinol, (R)-(+)-3-piperidinol, or (R)-(+)-3-pyrrolidinol. Amine substituents included alkyl and aralkyl groups. In vitro Ki values ranged from 0.05 nM to >100 nM. (R)-N-(2-Fluoroethyl)-3-piperidyl benzilate (3-FEPB, 22, Ki = 12.1 nM) and N-(2-fluoroethyl)-4-piperidyl benzilate (4-FEPB, 8, Ki = 1.83 nM) were selected for radiolabeling with fluorine-18. Using alkylation with 2-[18F]fluoroethyl triflate, 3-[18F]FEPB (42) and 4-[18F]-FEPB (43) were produced in 7-9% radiochemical yield and >97% radiochemical purity. For in vivo studies, retention was moderate in mouse brain for 42; however, blocking with scopolamine showed that uptake was not muscarinic cholinergic receptor-mediated. Conversely, 43 exhibited high, receptor-mediated retention in mouse brain, with significant clearance after 1 h. These results suggest that 43 could have applications as an in vivo probe for measuring endogenous acetylcholine levels.