42856-71-3

Basic information

• Product Name: (S)-2-Methylproline
• Synonyms: (S)-2-Methyl proline;(2s,5s)-5-Methylpyrrolidine-2-Carboxylic Acid;5-Methyl-L-Proline;(2S)-2-Methylpyrrolidin-2-ylcarboxylic acid;L-Proline, 2-methyl- (9CI);(S)-2-methylpyrrolidine-2-carboxylic acid;α-methyl-l-proline;2-methylproline
• CAS NO: 42856-71-3
• Molecular Formula: C₆H₁₁NO₂
• Molecular Weight: 129.16
• EINECS: 1592732-453-0
• Product Categories: GLYCINESCAFFOLD;Peptide Synthesis;Proline Derivatives;Unnatural Amino Acid Derivatives
• Mol File: 42856-71-3.mol
• Article Data: 14

Chemical Properties

• Melting Point: 310°C(lit.)
• Boiling Point: 241.9 °C at 760 mmHg
• Flash Point: 100.1 °C
• Appearance: /
• Density: 1.119 g/cm³
• Vapor Pressure: 0.0116mmHg at 25°C
• Refractive Index: 1.475
• Storage Temp.: -15°C
• Solubility: soluble in Methanol
• PKA: 2.44±0.20(Predicted)
• BRN: 4350211
• CAS DataBase Reference: (S)-2-Methylproline(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-Methylproline(42856-71-3)
• EPA Substance Registry System: (S)-2-Methylproline(42856-71-3)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 42856-71-3(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C6H11NO2/c1-6(5(8)9)3-2-4-7-6/h7H,2-4H2,1H3,(H,8,9)/t6-/m1/s1

Upstream product

• 86046-11-9 (2R,5S)-2-tert-butyl-5-methyl-1-aza-3-oxabicyclo<3.3.0>octan-4-one 
• 66856-17-5 2-amino-5-hydroxy-2-methylpentanoic acid 
• 160187-05-3 (S)-2-amino-5-hydroxy-2-methylpentanoic acid 
• 147-85-3 L-proline 
• 118916-60-2 (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one 
• 1415303-35-3 1-(carbamoyl phenylmethyl)-2-cyano-2-methylpyrrolidine 
• 103336-06-7 N-(tert-butoxycarbonyl)-2-methyl-L-proline 
• 1415303-22-8 (2S,1'S)-N-(1'-phenylethyl)-α-methylprolinamide 
• 111080-58-1 1-benzyl-2-methylpyrrolidine-2-carboxamide 
• 1310563-79-1 1-benzyl-2-methylpyrrolidine-2-carbonitrile 
• 1415303-16-0 tert-butyl 2-carbamoyl-2-methylpyrrolidine-1-carboxylate 
• 144688-73-3 N-tert-butoxycarbonyl-α-cyano-α-methylpyrrolidine 
• 5891-21-4 5-chloro-2-pentanone 
• 848488-83-5 DL-(α-methyl)proline amide 

Downstream Products

• 88958-64-9 1-(4-nitrophenyl)-1-hydroxy-3-butanone 
• 1339022-10-4 tert-butyl (2S)-2-(hydroxymethyl)-2-methylpyrrolidine-1-carboxylate 
• 152722-89-9 (2R,4R)-4-Hydroxy-2-methylprolin 
• 1261569-85-0 (S)-8a-methyloctahydropyrrolo[1,2-a]pyrazine 
• 847952-36-7 (8aS)-8a-methylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 1374892-64-4 (S)-2-methyl-pyrrolidine-1,2-dicarboxylic acid 1-methyl ester 
• 220060-17-3 (S)-1-tert-butyl 2-methyl 2-methylpyrrolidine-1,2-dicarboxylate 

Relevant articles and documents

Preparation method of optically active 2-methylproline

The invention discloses a preparation method of optically active 2-methylproline. According to the method, 5-hydroxy-2-pentanone (formula 1) is taken as a starting material to be subjected to condensation with a cyaniding reagent; hydrolysis is carried out so as to obtain 2-amino-5-hydroxy-2-methylvaleric acid (formula 2); 2-amino-5-hydroxy-2-methylvaleric acid (formula 2) and a resolving agent are subjected to salifying precipitation, followed by ph regulation and precipitation so as to obtain 2-amino-5-hydroxy-2-methylvaleric acid (formula 4) with optical activity; the compound as shown in formula 4 is protected with an amino protective agent to obtain a compound as shown in formula 5; the compound as shown in formula 5 is chlorinated with a chlorinating reagent while removing an amino protective group to obtain a compound as shown in formula 6; and one-pot cyclization is carried out to obtain the optically active 2-methylproline (formula 7). The preparation method is high in comprehensive yield, low in cost, mild in reaction condition and easy for large-scale production.

Α-substd. provitamin optically active production of phosphorus

PROBLEM TO BE SOLVED: To provide an industrial method practically suitable for producing an optically active α-substituted prolines with short process and mild conditions.SOLUTION: A method of producing an optically active α-substituted prolines (6) includes (d) a step of obtaining an optically active N, α-substituted prolines (5) by hydrolysis of an optically active N, α-substituted proline amides (4), and (e) a step of obtaining an optically active α-substituted prolines (6) by eliminating the optically active N, and a protective group Rof the α-substituted prolines (5).

PROCESS FOR PRODUCING SOLID AMINO ACID

The problem to be solved by the present invention is to ea lily and efficiently produce an amino acid having 2 to 7 carbon atoms as a high-purity solid without complicated operation, which is useful as a synthetic intermediate for medicines or agrochemicals. The present invention is characterized in comprising a step of precipitating solid amino acid with high purity. In the present invention, the by-produced salt composed of the sulfonic acid and the amine was removed to the mother liquor by reacting an amine with a sulfonic acid salt of amino acid in an aprotic polar solvent, or by reacting a sulfonic acid with an amine salt of amino acid in an aprotic polar solvent. The sulfonic acid salt of amino acid, for example, may be produced by reacting a N-(tert-butoxycarbonyl) amino acid with a sulfonic acid, or by reacting an amino acid tert-butyl ester with a sulfonic acid.