101930-07-8

Basic information

• Product Name: (R)-(+)-1-Benzyl-3-pyrrolidinol
• Synonyms: (R)-3-HYDROXYPYRROLIDINE, N-BENZYL;(r)-3-hydroxy-1-benyzl-pyrrolidine;(R)-3-HYDROXY-1-BENZYL-PYRROLIDINE;(R)-1-BENZYL-PYRROLIDIN-3-OL;(R)-1-N-BENZYL-3-HYDROXYPYRROLIDINE;(R)-(+)-1-BENZYL-3-PYRROLIDINOL;(R)-1-BENZYL-3-PYRROLIDINOL;(R)-1-BENZYL-3-HYDROXYPYRROLIDINE
• CAS NO: 101930-07-8
• Molecular Formula: C₁₁H₁₅NO
• Molecular Weight: 177.24
• EINECS: 212-273-5
• Product Categories: Pyrrole&Pyrrolidine&Pyrroline;Benzenes;Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry;Chiral Building Blocks;Heterocyclic Building Blocks;Pyrrolidines
• Mol File: 101930-07-8.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 116 °C0.9 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.07 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000592mmHg at 25°C
• Refractive Index: n20/D 1.548(lit.)
• Storage Temp.: 2-8°C
• PKA: 14.82±0.20(Predicted)
• CAS DataBase Reference: (R)-(+)-1-Benzyl-3-pyrrolidinol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-1-Benzyl-3-pyrrolidinol(101930-07-8)
• EPA Substance Registry System: (R)-(+)-1-Benzyl-3-pyrrolidinol(101930-07-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 101930-07-8(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow to gold to brown liquid

Uses

(R)-(+)-1-Benzyl-3-pyrrolidinol, is a chiral building block used for the synthesis of various pharmaceutical and biologically active compounds. It can be used for the preparation of beta-proline like derivatives, acting as sodium channel blockers

InChI:InChI=1/C11H15NO/c13-11-6-7-12(9-11)8-10-4-2-1-3-5-10/h1-5,11,13H,6-9H2/t11-/m1/s1

Upstream product

• 6913-92-4 1-benzyl-2,5-dihydro-1H-pyrrole 
• 29897-82-3 N-benzylpyrrolidine 
• 100-46-9 benzylamine 
• 100-44-7 benzyl chloride 
• 104706-47-0 (R)-3-hydroxypyrrolidine hydrochloride 
• 1246182-92-2 (R)-1-benzyl-3-pyrrolidine-3-d 
• 165657-63-6 (3R)-1-benzyl-3-hydroxypyrrolidine-2,5-dione 
• 775-16-6 N-benzyl-3-pyrrolidinone 
• 122929-12-8 rac-N-benzyl-3-pyrrolidinyl acetate 
• 775-15-5 1-benzyl-3-pyrrolidinol 
• 1227263-77-5 (3S)-1-[(2-aminophenyll)methyl]pyrrolidin-3-ol 
• 6159-55-3 (+)-vasicinol 
• 921202-52-0 (2S,3R)-1-benzyl-2-vinylpyrrolidin-3-ol 
• 1104643-29-9 (R)-3-tert-butoxy-N-benzylpyrrolidine 

Downstream Products

• 109431-87-0 (R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate 
• 315191-14-1 Hydroxy-diphenyl-acetic acid (R)-1-benzyl-pyrrolidin-3-yl ester 
• 719278-67-8 (3S)-1-benzylpyrrolidin-3-yl-(2R)-hydroxy(3-oxocyclopentyl)phenyl acetate 
• 183540-37-6 1-Benzyl-3-(R)-tetrahydropyranyloxypyrrolidine 
• 128510-52-1 benzoic acid (S)-1-benzyl-pyrrolidin-3-yl ester 
• 1246182-99-9 (S)-1-benzyl-3-bromopyrrolidine 
• 870859-01-1 (S)-(1-benzyl-pyrrolidin-3-yl)-[(R)-1-(3-methoxyphenyl)ethyl]amine 
• 116143-02-3 (3R)-1-(phenylmethyl)pyrrolidin-3-ol Acetate 
• 775-16-6 N-benzyl-3-pyrrolidinone 
• 204973-04-6 (S)-1-benzyl-3-chloropyrrolidine 
• 872030-39-2 5-((S)-1-benzyl-pyrrolidin-3-yloxy)-1H-indole-2-carboxylic acid ethyl ester 
• 791119-33-0 (R)-1-benzyl-3-(4,4'-dichlorobenzhydryloxy)pyrrolidine 
• 169749-99-9 (3S)-(-)-1-benzyl-3-(methylamino)pyrrolidine 
• 69478-77-9 ((S)-1-Benzyl-pyrrolidin-3-yl)-dimethyl-amine 

Relevant articles and documents

Exploring Derivatives of Quinazoline Alkaloid l-Vasicine as Cap Groups in the Design and Biological Mechanistic Evaluation of Novel Antitumor Histone Deacetylase Inhibitors

l-Vasicine is a quinazoline alkaloid with an electron dense ring and additional functionalities in its structure. Employing target oriented synthesis (TOS) based on in silico studies, molecules with significant docking scores containing different derivatives of l-vasicine as caps were synthesized. Interestingly, one molecule, i.e., 4a, which contained 3-hyroxypyrrolidine as a cap group and a six carbon long aliphatic chain as a linker was found to inhibit HDACs. 4a showed more specificity toward class I HDAC isoforms. Also 4a was found to be less cytotoxic toward normal cell lines as compared to cancer cell lines. 4a inhibited cancer cell growth and induced cell death by various mechanisms. However, 4a was found to induce cell death independent of ROS generation, and unlike many natural product based HDAC inhibitors, 4a was found to be nontoxic under in vivo conditions. Importantly, we for the first time report the possibility of using a 3-hydroxypyrrolidine cap for the synthesis of HDAC inhibitors with good potency.

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.

Natural (-)-vasicine as a novel source of optically pure 1-benzylpyrrolidin-3-ol

A facile and scalable methodology for the preparation of optically active (3S)-1-benzylpyrrolidin-3-ol (3), an important drug precursor, is reported. Starting from the naturally occurring alkaloid (-)-vasicine (1), a major alkaloid of the plant Adhatoda vasica, 3 was obtained in 84% overall yield (Scheme 3). Copyright