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

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

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

• 13220-33-2 1-methyl-3-pyrrolidinol 
• 215854-01-6 (S)-3-(benzyloxy)-1-methylpyrrolidine-2,5-dione 
• 1562400-53-6 C₁₃H₁₇NO₄ 
• 207856-85-7 (3S)-1-methylpyrrolidin-3-yl (2R)-2-cyclopentyl-2-hydroxy-2-phenylacetate 
• 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 
• 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 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.

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.

Isothiazolecarboxylic acid derivatives and their use as microbicides

Novel isothiazolecarboxylic acid derivatives of the formula (I), in which A, Q, Z and k have the meanings mentioned in the specification, processes for the preparation of the new compounds and their use as microbicides.

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.

Die Startereinheit der Rapamycin-Polyketid-Synthase

Keywords: Biosynthesen; Polyketide; Rapamycin

OBSERVATIONS REGARDING ESCHENMOSER SULFIDE CONTRACTIONS OF Β-OXIGENATED THIOLACTAMS

Application of an Eschenmoser sulfide contraction to a thiolactam bearing a β-acyloxy group was complicated by a competitive β-elimination reaction.Changing the β-substituent to an alkoxy group retarded the rate of elimination such that sulfide contraction products could be obtained.

Optical Isomers of Rocastine and Close Analogues: Synthesis and H1 Antihistaminic Activity of Its Enantiomers and Their Structural Relationship to the Classical Antihistamines

The enantiomers of 2--3,4-dihydro-4-methylpyrido-1,4-oxazepine-5(2H)-thione (rocastine) and two of its more potent analogues were prepared with an enantiomeric purity of > 99.9percent.The antihistaminic activity of these compounds was assessed by their ability to block histamine-induced lethality in guinea pigs and to inhibit mepyramine binding to guinea pig cortex.In this series, compounds having the R configuration at the 2-position are at least 300 times more potent than the S isomers.Conformational analysis and molecular modeling suggest that rocastine can adopt a conformation in which the pyridine ring, ether oxygen, and protonated amine functions are positioned similarly to the corresponding elements of the probable binding conformers of some of the more classical antihistamines.This conformation, boatlike in the oxazepine ring with the side chain quasi-equatorial and folded back toward the ring, is the likely binding conformer at the histamine H1 receptor, and the available structure-activity relationship data is consistent with this interpretation.

N-SUBSTITUTED HYDROXYSUCCINIMIDES FROM (S)-MALIC ACID AS NEW REAGENTS FOR ASYMMETRIC DIELS-ALDER ADDITION TO ENOATES

(S)-N-Methyl-2-hydroxysuccinimide, easily available from natural (S)-malic acid, supplements the previously introduced (R)-pantolactone as chiral auxiliary for asymmetric Diels-Alder reactions of enoates, but yields products of opposite configuration.Practical large-scale preparations of enantiomer pairs of synthetically important Diels-Alder adducts, including adducts from crotonates, are described.

Fused aromatic oxazepinones, thiazepinones, diazepinones and sulfur analogs thereof

Aromatic azepinones and thiones having the formula STR1 wherein; A is benzene, naphthalene, quinoline or pyridine; B is oxygen or sulfur; E is oxygen, sulfur or STR2 n is 1, 2 or 3; Z is an amino or a heterocyclic nitrogen-containing radical; R is hydrogen, loweralkyl, cycloalkyl or phenylloweralkyl; Y is halo, loweralkyl, loweralkoxy, diloweralkylamino, nitro, amino, loweracetylamino, trifluoromethyl, phenyl or phenyl substituted by one to three Y' radicals selected from halo, loweralkyl, loweralkoxy, diloweralkylamino, nitro, amino, loweracylamino or trifluoromethyl; and having antihistaminic utility, a process for the preparation thereof and chemical intermediates therefor are disclosed.