104612-35-3

Basic information

• Product Name: (S)-(-)-2-HYDROXY-N-METHYLSUCCINIMIDE
• Synonyms: (S)-(-)-2-HYDROXY-N-METHYLSUCCINIMIDE;S(-)-3-HYDROXY-1-METHYL-2,5-PYRROLIDINEDIONE;(S)-(-)-2-HYDROXY-N-METHYLSUCCINIMIDE, 9 7%;(S)-N-Methylhydroxysuccinimide;(S)-3-hydroxy-1-methylpyrrolidine-2,5-dione;(3S)-3-Hydroxy-1-Methyl-2,5-pyrrolidinedione;(S)-(-)-2-Hydroxy-N-methylsuccinimide 97%
• CAS NO: 104612-35-3
• Molecular Formula: C₅H₇NO₃
• Molecular Weight: 129.11
• EINECS: 200-258-5
• Product Categories: Chiral Compound;Chiral Reagents;Miscellaneous Reagents
• Mol File: 104612-35-3.mol
• Article Data: 11

Chemical Properties

• Melting Point: 82-87 °C(lit.)
• Boiling Point: 314.9°Cat760mmHg
• Flash Point: 144.3°C
• Appearance: /
• Density: 1.438g/cm³
• Vapor Pressure: 3.87E-05mmHg at 25°C
• Refractive Index: 1.549
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• PKA: 11.25±0.20(Predicted)
• CAS DataBase Reference: (S)-(-)-2-HYDROXY-N-METHYLSUCCINIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-2-HYDROXY-N-METHYLSUCCINIMIDE(104612-35-3)
• EPA Substance Registry System: (S)-(-)-2-HYDROXY-N-METHYLSUCCINIMIDE(104612-35-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 104612-35-3(Hazardous Substances Data)

Usage

Description

(S)-(-)-2-HYDROXY-N-METHYLSUCCINIMIDE, also known as a Hydroxysuccinimide derivative, is a light yellow solid with unique chemical properties. It is a compound that plays a significant role in various chemical reactions and applications due to its chiral nature and reactivity.

Uses

Used in Asymmetric Synthesis:
(S)-(-)-2-HYDROXY-N-METHYLSUCCINIMIDE is used as a chiral auxiliary for enhancing the diastereomeric excess of the Diels-Alder adducts formed in asymmetric Diels-Alder reactions. This application is crucial in the synthesis of enantiomerically pure compounds, which are essential in the pharmaceutical industry for the development of drugs with specific biological activities.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (S)-(-)-2-HYDROXY-N-METHYLSUCCINIMIDE is used as a key intermediate in the synthesis of various drugs and drug candidates. Its chiral properties allow for the creation of specific drug molecules with desired biological activities and reduced side effects.
Used in Chemical Research:
(S)-(-)-2-HYDROXY-N-METHYLSUCCINIMIDE is also utilized in chemical research as a reagent for various organic reactions. Its unique structure and properties make it a valuable tool for understanding reaction mechanisms and developing new synthetic methods.
Used in Material Science:
In the field of material science, (S)-(-)-2-HYDROXY-N-METHYLSUCCINIMIDE can be used as a building block for the development of novel chiral materials with specific properties, such as optical activity or selectivity in catalysis.
Overall, (S)-(-)-2-HYDROXY-N-METHYLSUCCINIMIDE is a versatile compound with a wide range of applications across different industries, including pharmaceuticals, chemical research, and material science, due to its unique chemical properties and chiral nature.

InChI:InChI=1/C5H7NO3/c1-6-4(8)2-3(7)5(6)9/h3,7H,2H2,1H3/t3-/m0/s1

Upstream product

• 97-67-6 (S)-Malic acid 
• 74-89-5 methylamine 
• 171021-07-1 (S)-1-methyl-2,5-dioxopyrrolidin-3-yl acetate 
• 617-48-1 malic acid 

Downstream Products

• 1562400-53-6 C₁₃H₁₇NO₄ 
• 207856-85-7 (3S)-1-methylpyrrolidin-3-yl (2R)-2-cyclopentyl-2-hydroxy-2-phenylacetate 
• 13220-33-2 1-methyl-3-pyrrolidinol 
• 171232-17-0 ((2S,3S,5S)-3-Benzyloxy-5-methoxycarbonylmethyl-1-methyl-pyrrolidin-2-yl)-acetic acid methyl ester 
• 171021-15-1 ((2S,3S)-3-Benzyloxy-1-methyl-5-thioxo-pyrrolidin-2-yl)-acetic acid methyl ester 
• 171021-14-0 ((2S,3S)-3-Benzyloxy-1-methyl-5-oxo-pyrrolidin-2-yl)-acetic acid methyl ester 
• 171021-13-9 (4S,5S)-5-Allyl-4-benzyloxy-1-methyl-pyrrolidin-2-one 
• 215854-02-7 (S)-5-Benzyl-4-benzyloxy-5-hydroxy-1-methyl-pyrrolidin-2-one 
• 215854-04-9 (-)-(4S,5R)-5-benzyl-4-benzyloxy-1-methyl-2-pyrrolidinone 
• 215854-01-6 (S)-3-(benzyloxy)-1-methylpyrrolidine-2,5-dione 
• 104641-59-0 (3S)-1-methylpyrrolidin-3-ol 

Relevant articles and documents

Preparation method of 1-methyl-3-pyrrolidinol

The invention relates to the technical field of synthesis of medical intermediates, and particularly discloses a preparation method of 1-methyl-3-pyrrolidinol. The preparation method comprises the following steps that S1, a compound I and a compound II are subjected to a ring closing reaction, so a compound III is obtained; and S2, the compound III obtained in the step S1 and a reducing agent IV are subjected to a reduction reaction, so 1-methyl-3-pyrrolidinol is obtained, wherein the compound I, the compound II and the compound III are as shown in the specification; and the reducing agent IV is one or more selected from a group consisting of sodium borohydride, potassium borohydride, boron trifluoride-diethyl ether and boron tribromide-diethyl ether. According to the preparation method, the compound II and the compound I are selected and subjected to the ring closing reaction to obtain the intermediate compound III, and the compound III is solid and is easy to crystallize and purify, so the purification difficulty of the intermediate is reduced, the purity of the intermediate is favorably improved, and the product quality of the 1-methyl-3-pyrrolidinol is further improved.

SYNTHESIS OF AN ANTIVIRAL COMPOUND

The present disclosure provides a processes for the preparation of a compound of Formula I: which is useful as an antiviral agent. The disclosure also provides compounds that are synthetic intermediates to compounds of Formula I.

An easy access to protected (4S, 5R)-5-alkyl-4-hydroxy-2-pyrrolidinones and their use as versatile synthetic intermediates

A versatile approach to enantiopure (4S, 5R)-5-alkyl-4-hydroxy-2- pyrrolidinones is described. The key steps involve a regioselective Grignard reagent addition to (S)-malimides, and diastereoselective reductive dehydroxylation of the resulting hemi-azaketals. The flexibility of this methodology has been demonstrated by the synthesis of (2R, 3R)-3-amino-1- benzyl-2-methylpyrrolidine, the parent diamine of antipsychotic agent, emonapride, and the unnatural enantiomer of the β-hydroxy-γ-amino acid residue of hapalosin in lactam form.