83220-72-8

Basic information

• Product Name: DL-3-PYRROLIDINOL
• Synonyms: pyrrolidinol;DL-3-PYRROLIDINOL 95+%;rac-(3R*)-Pyrrolidine-3-ol;rac-Pyrrolidine-3α*-ol;(3as,3bs,5ar,7r,9as,9bs,11as)-2-amino-7-hydroxy-9a,11a-dimethyl-3,3a,3b,4,5,5a,6,7,8,9,9a,9b,11,11a-tetradecahydro-10h-naphtho[2,1-e]indol-10-one;3-HYDROXYPYRROLINE;DL-3-PYRROLIDINOL;DL-3-HYDROXYPYRROLIDINE
• CAS NO: 83220-72-8
• Molecular Formula: C₄H₉NO
• Molecular Weight: 87.12
• EINECS: 254-944-5
• Mol File: 83220-72-8.mol

Chemical Properties

• Boiling Point: 108-110 °C8 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.076 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.49(lit.)
• CAS DataBase Reference: DL-3-PYRROLIDINOL(CAS DataBase Reference)
• NIST Chemistry Reference: DL-3-PYRROLIDINOL(83220-72-8)
• EPA Substance Registry System: DL-3-PYRROLIDINOL(83220-72-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37
• WGK Germany: 3
• F: 10-34
• HazardClass: IRRITANT
• Hazardous Substances Data: 83220-72-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
DL-3-Pyrrolidinol is used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides.
Used in Organic Chemistry:
DL-3-Pyrrolidinol serves as a chiral auxiliary in organic chemistry, aiding in the synthesis of enantiomerically pure compounds, which is crucial for the production of pharmaceuticals with desired biological activities.
Used in Solvent Production:
DL-3-Pyrrolidinol is a potential precursor for the production of N-methylpyrrolidone, a versatile solvent used in various industrial applications, including paint and coating formulations, adhesives, and cleaning agents.
Used in Chiral Building Blocks for Biologically Active Compounds:
DL-3-Pyrrolidinol has been studied for its potential as a chiral building block in the synthesis of biologically active compounds, which could lead to the development of new drugs with improved efficacy and selectivity.

Upstream product

• 101469-91-4 (3S)-1-benzyl-3-hydroxypyrrolidine-2,5-dione 
• 51-35-4 4R-4-hydroxyproline 
• 101385-90-4 (R)-N-benzyl-3-hydroxypyrrolidine 
• 30724-02-8 (4R)-4-hydroxyproline 
• 107-21-1 ethylene glycol 
• 74957-62-3 (R)-3-hydroxy-4-(methanesulfonyloxy)butyronitrile 
• 84367-31-7 (R)-γ-chloro-β-hydroxybutyronitrile 
• 177948-70-8 (3R)-N(H)-3-(benzyloxy)pyrrolidine 
• 480452-55-9 (R)-3-tert-butyldimethylsilyloxy-pyrrolidine hydrochloride 
• 36901-86-7 cis-hydroxy-D-proline 

Downstream Products

• 100858-33-1 (3R)-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester 
• 125787-05-5 (3R)-1-methoxycarbonylpyrrolidin-2-ol 
• 101385-90-4 (R)-N-benzyl-3-hydroxypyrrolidine 
• 109431-87-0 (R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate 
• 51-35-4 4R-4-hydroxyproline 
• 916733-17-0 (R)-1-(3-hydroxypyrrolidin-1-yl)ethan-1-one 
• 216666-99-8 (R)-1-(2-methoxyethyl)-3-hydroxypyrrolidine 
• 216667-19-5 (R)-1-(o-methoxyphenylmethyl)-3-hydroxypyrrolidine 
• 448236-06-4 (R)-N-[N-(tert-butoxycarbonyl)-L-phenylalanyl]pyrrolidin-3-ol 
• 181959-79-5 (R)-N-(p-nitrophenyl)-3-hydroxypyrrolidine 

Relevant articles and documents

Synthesis method of (R)-3-hydroxypyrrolidine

The invention relates to the technical field of organic synthesis, in particular to a synthesis method of (R)-3-hydroxy pyrrolidine, which comprises the following steps: reacting Lhydroxyproline in a reaction medium at 80-160 DEG C under the action of a decarboxylation catalyst, and carrying out reduced pressure distillation after the reaction is completed, thereby obtaining the (R)-3-hydroxy pyrrolidine, and the carboxylic acid decarboxylation catalyst is selected from methyl isobutyl or cyclohexanone. The (R)-3-hydroxy pyrrolidine synthesis method provided by the invention uses the cheap, safe and non-toxic decarboxylation catalyst and the reaction medium which is easier to recover, achieves higher yield than the prior art, and is suitable for industrial large-scale production.

Redox Condensations of o-Nitrobenzaldehydes with Amines under Mild Conditions: Total Synthesis of the Vasicinone Family

A total synthesis of the vasicinone family of natural products from bulk chemicals was developed. Reductive condensation of o-nitrobenzaldehydes with amines utilizing iron pentacarbonyl as a reducing agent followed by subsequent oxidation leads to a great variety of polycyclic nitrogen-containing heterocycles under mild conditions. Enantiomerically pure vasicinone, rutaecarpine, isaindigotone, and luotonin were synthesized from readily available starting materials like hydroxyproline, nitrobenzaldehyde, pyrrolidine, and piperidine in two to four operational steps without chromatography. The antifungal activity of all products was tested.

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 PROCESS FOR THE PREPARATION OF (3SM-[2-(2 J-DIHYDRO-5- BENZOFURANYL?ETHYL]-α.α -DIPHENYL-3-PYRROLIDINEACETAMIDE HYDROBROMIDE

The present invention is directed to a novel, industrially viable and cost effective process for manufacturing (3 S)- 1 -[2-(2,3-Dihydro-5-benzofuranyl)ethyl]-a,a-diphenyl-3-pyrrolidineacetamide hydrobromide also known as Darifenacin hydrobromide.

IMPROVED PROCESS FOR PRODUCING DARIFENACIN

The present invention discloses an improved process for producing darifenacin, the process comprising decarboxylating (2S,4R)-4-hydroxy-2-pyrrolidine carboxylic acid followed by in situ tosylation to give l-tosyl-3-(R)-(-)-hydroxypyrrolidine, tosylating the l-tosyl-3-(R)-(-)-hydroxypyrrolidine with methyl-p-toluenesuolphonate to give l-tosyl-3- (S)-(-)-tosyloxy pyrrolidine, reacting l-tosyl-3-(S)-(-)-tosyloxy pyrrolidine with diphenyl acetonitrile in presence of a base to give 3-(S)-(+)-(l-cyano-l,l-diphenylmethyl)-l- tosylpyrrolidine, de-protecting 3-(S)-(+)-(l-cyano-l,l-diphenylmethyl)-l- tosylpyrrolidine in the presence of phenol in acidic medium to give 3-(S)-(+)-(l-cyano- 1,1-diphenylmethyl) pyrrolidine, hydrolyzing 3-(S)-(+)-(l-cyano-l,l-diphenylmethyl) pyrrolidine followed by salt formation to obtain 3-(S)-(+)-(l-carbamoyl-l,l- diphenylmethyl)pyrrolidine.L-(+)-tartrate, condensing 3-(S)-(+)-( 1 -carbamoyl- 1,1- diphenylmethyl)pyrrolidine-L(+)-tartrate with 5-(2-bromoethyl)-2,3-dihydrobenzofuran employing a base in a solvent to give darifenacin.

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.

Syntheses of ureas

The present invention provides intermediates, synthetic methods and novel urea compositions of matter.

Process for preparing amines

A process for preparing an amine which comprises in preparing an amine by decarboxylating an α-amino acid under heating in a high boiling liquid polymer having average molecular weight 200 to 6000, and directly recovering this amine by distillation in the same reaction system, namely in one pot.

Process for preparing optically active 1- (4-nitrophenyl) -3-pyrrolidinol derivatives, and chiral para-phenylenediamines containing a pyrrolidinyl group

A process for preparing an optically active 1-(4-nitrophenyl)-3-pyrrolidinol derivative corresponding to formula (I) below: para-Phenylenediamine derivatives substituted by a chiral pyrrolidinyl group, of formula (II), and their addition salts: A dyeing composition comprising a para-phenylenediamine derivative of formula (II). A method of oxidation-dyeing keratin fibers which employs said composition. Multicompartment devices in which a first compartment contains the said dyeing composition and a second compartment contains an oxidizing agent.