217449-25-7

Basic information

• Product Name: (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol hydrochloride
• Synonyms: (3R, 4R)-4-Hydroxymethyl-pyrrolidin-3-ol hydrochloride;3-PYRROLIDINEMETHANOL, 4-HYDROXY HYDROCHLORIDE (1:1), (3R,4R)-
• CAS NO: 217449-25-7
• Molecular Formula: C₅H₁₂ClNO₂
• Molecular Weight: 153.6073
• Mol File: 217449-25-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 268.1°C at 760 mmHg
• Flash Point: 156.7°C
• Vapor Pressure: 0.00105mmHg at 25°C
• CAS DataBase Reference: (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol hydrochloride(217449-25-7)
• EPA Substance Registry System: (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol hydrochloride(217449-25-7)

Safety Data

• Hazardous Substances Data: 217449-25-7(Hazardous Substances Data)

Usage

General Description

(3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol hydrochloride is a chemical compound that belongs to the class of pyrrolidin-3-ols. It contains a hydroxymethyl group and a hydrochloride salt. (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol hydrochloride is a chiral molecule with stereocenters at positions 3 and 4. It is commonly used as a reagent in organic synthesis and as a precursor in the preparation of pharmaceuticals. (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol hydrochloride has potential applications in the pharmaceutical industry, particularly in the development of new drugs and therapeutic agents. Its unique structural properties make it a valuable building block for the synthesis of various bioactive compounds.

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Relevant articles and documents

A practical large-scale synthesis of (3R,4R)-4-(Hydroxymethyl)pyrrolidin-3- ol via asymmetric 1,3-dipolar cycloaddition

(3R,4R)-4-(Hydroxymethyl)pyrrolidin-3-ol (1), which is a useful intermediate for the synthesis of various bioactive molecules, has been synthesized in 51% overall yield by 1,3-dipolar cycloaddition reaction from the dipolarophile, (E)-3-benzyloxypropenoyl-(2′S)-bornane-10,2-sultam (5), and the achiral ylide precursor, N-(benzyl)-N-(methoxymethyl)-N- (trimethylsilylmethyl)amine (6), without using chromatography and the subsequent reduction with LAH and catalytic hydrogenation. The diastereomers 7 and 8 were separated by crystallization, and efficient procedures were developed for the subsequent reactions to afford 1.

Development of the Ireland-Claisen rearrangement of allyl-2-alkoxyacetate bearing an allylic amine and the transformation to 3-hydroxy-4- hydroxymethylpyrrolidine

An unprecedented Ireland-Claisen rearrangement of allylglycolate bearing an allylic amine was realized, affording the corresponding product with excellent diastereoselectivity and in high yield. The product was analyzed by X-ray crystallography, and demon

Process for the preparation of substituted pyrrolidine derivatives and intermediates

Two syntheses are provided; one for the preparation of (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol, and other for the preparation of (3S,4R)-4-(hydroxymethyl)pyrrolidin-3-ol. (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol is prepared using the achiral ylide prepared from benzylamine instead of phenethylamine (Scheme 3) which provides a crystalline intermediate. The synthesis of (3S,4R)-4-(hydroxymethyl)pyrrolidin-3-ol is achieved from (S)-diethylmalate as described in Scheme 4. A process for preparing camphor sultam is also provided.