177948-70-8

Basic information

• Product Name: (R)-3-BENZYLOXY-PYRROLIDINE
• Synonyms: pyrrolidine, 3-(phenylmethoxy)-, (3R)-
• CAS NO: 177948-70-8
• Molecular Formula: C₁₁H₁₅NO
• Molecular Weight: 177.24
• Mol File: 177948-70-8.mol

Chemical Properties

• Boiling Point: 269.2°C at 760 mmHg
• Flash Point: 106.7°C
• Appearance: /
• Density: 1.05g/cm³
• Vapor Pressure: 0.00737mmHg at 25°C
• Refractive Index: 1.545
• CAS DataBase Reference: (R)-3-BENZYLOXY-PYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-BENZYLOXY-PYRROLIDINE(177948-70-8)
• EPA Substance Registry System: (R)-3-BENZYLOXY-PYRROLIDINE(177948-70-8)

Safety Data

• Hazardous Substances Data: 177948-70-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-3-Benzyloxy-pyrrolidine is used as a chiral building block for the synthesis of various pharmaceuticals, contributing to the development of new drugs with improved efficacy and selectivity. Its stereochemistry plays a crucial role in the biological activity of the resulting compounds.
Used in Agrochemical Industry:
In the agrochemical sector, (R)-3-Benzyloxy-pyrrolidine serves as a chiral building block for the synthesis of agrochemicals, enhancing the effectiveness and selectivity of these compounds in pest control and crop protection.
Used in Fine Chemicals Industry:
(R)-3-Benzyloxy-pyrrolidine is utilized as a chiral building block in the synthesis of fine chemicals, which are high-purity chemicals used in various applications, including fragrances, flavors, and specialty chemicals.
Used in Catalyst and Ligand Development:
(R)-3-Benzyloxy-pyrrolidine is employed in the development of chiral catalysts and ligands for asymmetric synthesis, improving the efficiency and selectivity of chemical reactions, particularly in the synthesis of enantiomerically pure compounds.
Used in Biologically Active Molecule Production:
(R)-3-BENZYLOXY-PYRROLIDINE is used in the production of various biologically active molecules, which have potential applications in medicine, agriculture, and other fields due to their specific biological effects.
Used in Heterocyclic Compound Preparation:
(R)-3-Benzyloxy-pyrrolidine is utilized in the preparation of numerous heterocyclic compounds, which are an important class of organic compounds with diverse applications in pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C11H15NO/c1-2-4-10(5-3-1)9-13-11-6-7-12-8-11/h1-5,11-12H,6-9H2/t11-/m1/s1

Upstream product

• 196862-46-1 (R)-3-(benzyloxy)-4-chloro-butanenitrile 
• 100-39-0 benzyl bromide 
• 40499-83-0 (3R)-pyrrolidinol 
• 927819-90-7 (R)-3-(benzyloxy)pyrrolidine hydrochloride 
• 177947-67-0 (3R)-N-(tert-butyloxycarbonyl)-3-(benzyloxy)pyrrolidine 

Downstream Products

• 177947-68-1 (3R)-4-<3-(benzyloxy)pyrrolidin-1-yl>butanal dimethyl acetal 
• 40499-83-0 (3R)-pyrrolidinol 
• 927819-92-9 (R)-3-benzyloxypyrrolidine p-toluenesulfonate 
• 927819-95-2 3(R)-benzyloxypyrrolidine (L)-tartrate 
• 927819-96-3 3(R)-benzyloxypyrrolidine (D)-tartrate 
• 927819-97-4 3(R)-benzyloxypyrrolidine (L)-aspartate 
• 927819-94-1 (R)-3-benzyloxypyrrolidine benzoate 
• 927819-98-5 3(R)-benzyloxypyrrolidine (D)-aspartate 
• 927819-91-8 (R)-3-benzyloxypyrrolidine hydrobromide 
• 927819-93-0 (R)-3-benzyloxypyrrolidine sulfate 
• 927819-90-7 (R)-3-(benzyloxy)pyrrolidine hydrochloride 
• 900513-88-4 (1R,2R)-2-[(R)-3-(benzyloxy)pyrrolidin-1-yl]cyclohexanol 
• 1370354-77-0 C₂₇H₃₇NO₅ 
• 1370354-64-5 C₂₇H₃₇NO₅ 

Relevant articles and documents

A Recyclable Chiral 2-(Triphenylmethyl)pyrrolidine Organocatalyst Anchored to [60]Fullerene

Hybridization of a chiral 3-hydroxy-2-trityl-pyrrolidine deriving from (R)-pyrrolidinol with [60]fullerene via click chemistry provides a highly efficient supported enantioselective organocatalyst, which was successfully exploited in a Michael addition of

A fang chanfu law compound and its preparation method, pharmaceutical composition and use thereof

The invention relates to a new compound for conversion of auricular fibrillation, as shown in the general formula i in the specification (n in the formula is equal to 0 to 4), or pharmaceutically acceptable salt thereof. The invention also provides a novel compound used as a preventive medicine or therapeutic drug for atrial fibrillation, a preparation method and a pharmaceutical composition containing the compound.

NOVEL BETULINIC SUBSTITUTED AMIDE DERIVATIVES AS HIV INHIBITORS

The present invention relates to novel betulinic substituted amide compounds of formula (I); and pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4, R5, R6, R7, R8, X, Y, Z1, Z2, Z3 and are Formula (II) as defined herein. The invention novel betulinic substituted amide derivatives, related compounds, and pharmaceutical compositions useful for the therapeutic treatment of viral diseases and particularly HIV mediated diseases.

PROCESS FOR PRODUCTION OF ARALKYLOXYPYRROLIDINE DERIVATIVE

The present invention provides a process for producing a 3-aralkyloxypyrrolidine derivative which is important for production of pharmaceutical products and the like. In the present invention, a N-protected-3-hydroxypyrrolidine is converted into a N-protected-3-aralkyloxypyrrolidine by allowing an aralkyl halide to act in the presence of a base and at least one of a metal halide and a phase-transfer catalyst followed by deprotecting a N-protecting group to convert it to a 3-aralkyloxypyrrolidine derivative and subsequently treating the derivative in a solvent containing a polar solvent, thereby obtaining the 3-aralkyloxypyrrolidine derivative as a crystal. According to the present invention, a 3-aralkyloxypyrrolidine derivative of high purity can be produced conveniently and efficiently on an industrial scale.

PROCESS FOR PRODUCTION OF BENZYLOXYPYRROLIDINE DERIVATIVE, AND PROCESS FOR PRODUCTION OF HYDROCHLORIDE SALT POWDER OF OPTICALLY ACTIVE BENZYLOXYPYRROLIDINE DERIVATIVE

Provided are: a process for production of a benzyloxypyrrolidine derivative in high yield and safety, and a process for production of a hydrochloride powder of a benzyloxypyrrolidine derivative in high yield and safety; the process for production of a benzyloxypyrrolidine derivative expressed by the general formula (2) [Chemical formula 2], in reacting a pyrrolidinol derivative represented by the general formula (1) [Chemical formula 1 with a benzyl halide derivative in the presence of an alkali metal hydroxide, wherein the reaction is carried out in either of the following conditions A or B; condition A: an aprotic polar solvent, and condition B: an aliphatic ether solvent containing a phase transfer catalyst:

PROCESS FOR THE PREPARATION OF CHIRAL 3-HYDROXY PYRROLIDINE COMPOUND AND DERIVATIVES THEREOF HAVING HIGH OPTICAL PURITY

The present invention relates to an effective process for the preparation of optically pure chiral 3-hydroxypyrrolidine or derivatives thereof. More particularly, the present invention relates to an efficient process for the preparation of chiral 3-hydroxypyrrolidine or derivatives thereof, comprised of introducing a suitable protecting group to the starting material 4-chloro-3-hydroxybutyronitrile. Introduction of the hydroxy-protecting group provides advantages: efficient prevention of formation of side products, enhanced performance of the reduction of the nitrile group of the starting material, and enhanced performance of in-situ in? tramolecular cyclization. The chiral 3-hydroxypyrrolidine compound is produced in high yield and with high purity.

MERGED ION CHANNEL MODULATING COMPOUNDS AND USES THEREOF

Merged compounds of ion channel modulating compounds, including, for example, merged compounds of the ion channel modulating compound of the following formula: (I) are described herein, as well as methods of making and using such merged compounds and pharmaceutical compositions containing such merged compounds.

STEREOSELECTIVE SYNTHESIS OF 1,2-DISUBSTITUTED CYCLOALKYLS

A stereoselectively method of preparing a 1,2-disubstituted cycloalkyl, such as aminocycloalkyl ether compounds, from a trans-1,2-disubstituted cycloalkyl or a cis-2- substituted cycloalkanol. For example, a stereoselective method of preparing 1R-(3R-hydroxypyrrolidin-1-yl)-2R-(2-phenylethoxy)-cyclohexane from 1R,2R-cyclohexanediol or from meso-cis-1,2-cyclohexanediol is described. Aminocycloalkyl ethers, such as 1R-(3R-hydroxypyrrolidin-1-yl)-2R-(2-phenylethoxy)-cyclohexane, can be used to treat cardiac disease.

Synthesis and serotonergic activity of 3-[2-(pyrrolidin-1- yl)ethyl]indoles: Potent agonists for the h5-HT(1D) receptor with high selectivity over the h5-HT(1B) receptor

The design, synthesis, and biological evaluation of a novel series of 3- [2-(pyrrolidin-1-yl)ethyl]-indoles with excellent selectivity for h5-HT(1D) (formerly 5-HT(1Dα)) receptors over h5-HT(1B) (formerly 5-HT(1Dβ)) receptors are described. Clinically effective antimigraine drugs such as Sumatriptan show little selectivity between h5-HT(1D) and h5-HT(1B) receptors. The differential expression of h5-HT(1D) and h5-HT(1B) receptors in neural and vascular tissue prompted an investigation of whether a compound selective for the h5-HT(1D) subtype would have the same clinical efficacy but with reduced side effects. The pyrrolidine 3b was initially identified as having 9-fold selectivity for h5-HT(1D) over h5-HT(1B) receptors. Substitution of the pyrrolidine ring of 3b with methylbenzylamine groups gave compounds with nanomolar affinity for the h5-HT(1D) receptor and 100-fold selectivity with respect to h5-HT(1B) receptors. Modification of the indole 5-substituent led to the oxazolidinones 24a,b with up to 163-fold selectivity for the h5-HT(1D) subtype and improved selectivity over other serotonin receptors. The compounds were shown to be full agonists by measurement of agonist-induced [35S]GTPγS binding in CHO cells expressed with h5-HT receptors. This study suggests that the h5-HT(1D) and h5-HT(1B) receptors can be differentiated by appropriate substitution of the ligand in the region which binds to the aspartate residue and reveals a large binding pocket in the h5-HT(1D) receptor domain which is absent for the h5-HT(1B) receptor. The compounds described herein will be important tools to delineate the role of h5-HT(1D) receptors in migraine.