112348-45-5

Basic information

• Product Name: 1,2-Pyrrolidinedicarboxylic acid, 2-(2-propenyl)-, 1-(1,1-dimethylethyl) 2-methyl ester, (R)-
• CAS NO: 112348-45-5
• Molecular Formula: C14H23NO4
• Molecular Weight: 269.341
• Mol File: 112348-45-5.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: 1,2-Pyrrolidinedicarboxylic acid, 2-(2-propenyl)-, 1-(1,1-dimethylethyl) 2-methyl ester, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Pyrrolidinedicarboxylic acid, 2-(2-propenyl)-, 1-(1,1-dimethylethyl) 2-methyl ester, (R)-(112348-45-5)
• EPA Substance Registry System: 1,2-Pyrrolidinedicarboxylic acid, 2-(2-propenyl)-, 1-(1,1-dimethylethyl) 2-methyl ester, (R)-(112348-45-5)

Safety Data

• Hazardous Substances Data: 112348-45-5(Hazardous Substances Data)

Usage

Chemical Class

Pyrrolidine carboxylic acids

Stereoisomer

2-(2-propenyl)derivative of 1,2-pyrrolidinedicarboxylic acid

Common Usage

Organic synthesis and pharmaceutical research

Also Known As

(R)-baclofen

Receptor Interaction

GABA receptor agonist

Primary Use

Treatment of muscle spasticity

Additional Uses

Treatment of alcoholism and hiccups

Molecular Structure

Contains a pyrrolidine ring, carboxylic acid groups, and a 2-propenyl group

Chirality

(R)configuration at the stereocenter

Ester Functionality

2-methyl ester group present in the molecule

Upstream product

• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 
• 106-95-6 allyl bromide 
• 144085-23-4 N-tert-butoxycarbonyl-L-α-allylproline 
• 74-88-4 methyl iodide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 389127-43-9 (R)-methyl 2-allylpyrrolidine-2-carboxylate 
• 220200-87-3 (2R,5R)-5-(2-propenyl)-2-trichloromethyl-1-aza-3-oxabicyclo-[3.3.0]octane-4-one 
• 118916-60-2 (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one 
• 121772-98-3 (R)-2-allylpyrrolidine-2-carboxylic acid 
• 147-85-3 L-proline 
• 81286-82-0 (2R,5S)-2-tert-butyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one 
• 81286-83-1 (2R,5R)-5-allyl-2-tert-butyl-1-aza-3-oxabicyclo<3.3.0>octan-4-one 
• 186581-53-3 diazomethane 
• 43041-12-9 methyl pyrrolidine-2-carboxylate 

Downstream Products

• 144085-23-4 N-tert-butoxycarbonyl-L-α-allylproline 
• 441773-61-1 2-methoxycarbonylmethyl-2-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylmethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 112348-61-5 C₂₂H₂₄N₂O₅S 
• 112348-61-5 C₂₂H₂₄N₂O₅S 
• 112348-56-8 11-(methylthio)-11a-<2-hydroxy-3-<(p-tolylsulfonyl)-oxy>propyl>-1,2,3,11a-tetrahydro-5H-pyrrolo<2,1-c><1,4>benzodiazepin-5-one 
• 112348-47-7 N-(2-nitrobenzoyl)-2-(methoxycarbonyl)-2-(2-propenyl)pyrrolidine 
• 112348-48-8 2-Allyl-1-(2-amino-benzoyl)-pyrrolidine-2-carboxylic acid methyl ester 

Relevant articles and documents

Oxidative radical cyclizations of diketopiperazines bearing an amidomalonate unit. Heterointermediate reaction sequences toward the asperparalines and stephacidins

A novel approach to the diazabicyclo[2.2.2]octane core of prenylated bridged diketopiperazine alkaloids is described by direct oxidative cyclizations of functionalized diketopiperazines mediated by ferrocenium hexafluorophosphate or the Mn(OAc)3?2H2O/Cu(OTf)2 system. Divergent reaction pathways take place depending on the substitution pattern of the substrates and the oxidation conditions such as temperature or the presence or absence of persistent radical TEMPO. For ester-substituted diketopiperazines, the ester group exerts a significant influence on the reaction outcome and stereochemistry of the radical cyclizations.

A Convergent Synthesis of Enantiopure Open-Chain, Cyclic, and Fluorinated α-Amino Acids

A radical based synthesis of a broad variety of protected enantiopure α-amino acids, including fluorinated derivatives, is described. The radical addition furnishes naturally latent mercapto-α-amino acids ideally equipped for native chemical ligation.

Synthesis and evaluation of C8-substituted 4.5-spiro lactams as Glycogen Phosphorylase a inhibitors

An effective synthesis of 4.5-spiro lactams 28/29, has been completed in nine steps with an overall yield of 5.8%. The 4.5-spiro lactams were made from 2-allyl-Cbz-Pro-OMe 21, which was converted into the corresponding alcohol 22 via a hindered borane reaction with (2-methylbutyl)2borane. Subsequent Swern oxidation of 22 gave novel aldehyde 23. Aldehyde 23 was treated under Bucherer-Bergs reaction conditions to give hydantoin 26, which was opened to the corresponding amino acid 30 using di-tert-butyl dicarbonate and DMAP followed by hydrolysis. Treatment of amino acid 30 with acidic methanol gave 4.5-spiro lactams 28/29. Only 4.5-spiro lactam 29 displayed moderate activity against GPa with an IC50 of 241 μM.