135097-23-3

Basic information

• Product Name: 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-diMethylethyl) 2-ethyl ester, (2S)-
• Synonyms: 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-diMethylethyl) 2-ethyl ester, (2S)-;(S)-1-TERT-BUTYL 2-ETHYL PYRROLIDINE-1,2-DICARBOXYLATE
• CAS NO: 135097-23-3
• Molecular Formula: C₁₂H₂₁NO₄
• Molecular Weight: 243.29944
• Mol File: 135097-23-3.mol

Chemical Properties

• Boiling Point: 305.6±35.0 °C(Predicted)
• Appearance: /
• Density: 1.100±0.06 g/cm3(Predicted)
• PKA: -3.22±0.40(Predicted)
• CAS DataBase Reference: 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-diMethylethyl) 2-ethyl ester, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-diMethylethyl) 2-ethyl ester, (2S)-(135097-23-3)
• EPA Substance Registry System: 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-diMethylethyl) 2-ethyl ester, (2S)-(135097-23-3)

Safety Data

• Hazardous Substances Data: 135097-23-3(Hazardous Substances Data)

Usage

Derivative of

Pyrrolidine carboxylic acid

Common use

Intermediate in the synthesis of pharmaceuticals and agrochemicals

Chirality

Chiral molecule with a distinct three-dimensional structure

Enantiomerically pure compounds

Often used in the production of enantiomerically pure compounds

Applications

Organic chemistry and drug development

Structural properties

Unique structural properties and stereochemistry

Stereochemistry

(2S)configuration, indicating the arrangement of atoms in the molecule

Functional groups

Contains carboxylic acid, ester, and tertiary amine groups

Solubility

Likely soluble in organic solvents such as ethanol, methanol, or acetone, due to its nonpolar nature

Stability

Stable under normal conditions, but sensitive to heat, light, and moisture

Reactivity

May react with nucleophiles, acids, and bases, depending on the reaction conditions and reagents used

Purity

Often requires purification through techniques such as column chromatography or recrystallization to ensure enantiomeric purity

Safety

Handle with care, as it may have potential hazards depending on its use and concentration

Storage

Store in a cool, dry, and well-ventilated area, away from heat, light, and moisture, in a sealed container to maintain stability and purity

Upstream product

• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 75-03-6 ethyl iodide 
• 194594-23-5 5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 33305-75-8 L-proline ethyl ester monohydrochloride 
• 64-17-5 ethanol 
• 147-85-3 L-proline 
• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 
• 5817-26-5 ethyl (2S)-pyrrolidine-2-carboxylate 

Downstream Products

• 69610-41-9 Boc-L-Pro-H 
• 160115-24-2 (2S)-2-((dimethylamino)methyl)pyrrolidine-1-carboxylic acid tert-butyl ester 
• 1621435-13-9 tert-butyl 2-(((2S, 3R)-1, 3-bis (benzyloxy)-1-oxobutan-2-yl) carbamoyl)-2-(hydroxymethyl) pyrrolidine-1-carboxylate 
• 1621435-28-6 tert-butyl 2-((2S, 3R)-1, 3-bis (benzyloxy)-1-oxobutan-2-yl)-1-oxo-2, 5-diazaspiro [3.4] octane-5-carboxylate 
• 1194030-71-1 2-((benzyloxy)methyl)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid 
• 1621482-38-9 1-tert-butyl 2-ethyl 2-((benzyloxy)methyl)pyrrolidine-1,2-dicarboxylate 
• 33305-75-8 L-proline ethyl ester monohydrochloride 
• 92235-33-1 (S)-tert-butyl 2-(benzylcarbamoyl)pyrrolidine-1-carboxylate 
• 86661-32-7 (S)-tert-butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate 
• 135055-76-4 (S)-1-[(E)-3-(4-tert-Butyl-phenyl)-2-methyl-propenyl]-2-[(diphenylphosphanyl)-methyl]-pyrrolidine 
• 135055-75-3 (S)-(-)-N-tert-butoxycarbonyl-2-<(diphenylphosphino)methyl>pyrrolidine 
• 135055-77-5 (S)-2-[(Diphenylphosphanyl)-methyl]-1-((E)-2-methyl-but-1-enyl)-pyrrolidine 
• 130203-08-6 (E)-3-{(S)-2-[(Diphenylphosphanyl)-methyl]-pyrrolidin-1-yl}-2-methyl-but-2-enoic acid tert-butyl ester 
• 130203-07-5 (E)-3-{(S)-2-[(Diphenylphosphanyl)-methyl]-pyrrolidin-1-yl}-2-methyl-but-2-enoic acid ethyl ester 

Relevant articles and documents

ANTIVIRAL COMPOUNDS

The present disclosure provides compounds for treating a variety of diseases, such as respiratory syncytial virus (RSV), HRV, hMPV, ebola, Zika, West Nile, Dengue, and HCV.

A (1 R, 3 S) -3 - amino-cyclopentanol hydrochloride preparation method (by machine translation)

The invention discloses a (1 R, 3 S) - 3 - amino-cyclopentanol hydrochloride of the preparation method, the method using chiral carboxylic acid with hydroxylamine to form the amide as chiral source, in copper catalyzed oxidation in the reaction system to rapidly obtain a chiral Diels - alder reaction product, after passes through the reduction reaction and alkaline deprotection reaction, and acidified after reaction to obtain the target product. Chiral inducing reagent chiral carboxylic acid by simple acidification, extraction processing can be reclaimed and reused. This kind of (1 R, 3 S) - 3 - amino-cyclopentanol hydrochloride preparation method has high operation safety and high selectivity, raw materials are easy, and the cost is low, the reaction time is short and simple process flow and the like. (by machine translation)

Cobalt-Catalyzed Esterification of Amides

The first cobalt-catalyzed amide activation of N-Boc-amides, and their conversion into esters, is reported here. This new methodology presents a very practical process that does not require an inert atmosphere, uses an inexpensive cobalt catalyst, and proceeds under mild reaction conditions. This catalytic system has a broad substrate scope and has been shown to be highly efficient, with catalyst loadings as low as 1 mol %.

SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF

Disclosed are compounds having enhanced potency in the modulation of NMDA receptor activity. Such compounds are contemplated for use in the treatment of conditions such as depression and related disorders. Orally available formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.

One-pot transformation of carboxylic acids into nitriles

A variety of aromatic and aliphatic carboxylic acids were smoothly converted into the corresponding nitriles in good yields in a one-pot procedure by treatment with ethyl iodide/K2CO3/18-crown-6, followed by sodium diisobutyl-tert-butoxyaluminium hydride (SDBBA-H), and finally treatment with molecular iodine or 1,3-diiodo-5,5-dimethylhydantoin (DIH), and aqueous ammonia. This method is useful for the conversion of various aromatic and aliphatic carboxylic acids into the corresponding nitriles in a one-pot procedure. A variety of aromatic and aliphatic carboxylic acids were smoothly converted into the corresponding nitriles in good yields in a one-pot procedure by treatment with ethyl iodide/K2CO3/18-crown-6, followed by sodium diisobutyl-tert-butoxyaluminium hydride (SDBBA-H), and finally treatment with molecular iodine or 1,3-diiodo-5,5-dimethylhydantoin (DIH), and aqueous ammonia. Copyright

The Baylis-Hillman reaction with chiral α-amino aldehydes under racemization-free conditions

The Baylis-Hillman reaction with chiral α-amino aldehydes has been revisited. The reaction carried out under the influence of ultrasound avoids the aldehyde racemization almost completely, providing useful chiral substrates which can be used as starting materials for the synthesis of natural products. To demonstrate the synthetic applicability of these adducts, the easy preparation of a bicyclic lactam with an indolizidinic skeleton was accomplished. Georg Thieme Verlag Stuttgart.

The influence of conformational restriction in the C-terminus of growth hormone secretagogues on their potency

In order to obtain more potent growth hormone secretagogues, a comparison of ipamorelin and NN703 suggested the addition of a polar group at the C-terminus of NN703. A study was conducted using constrained amines for this purpose. Here, substituted 4-piperidinylamino- and 4-dimethylaminopiperidino-substitutents were found to give the most active compounds. A replacement of the 4-dimethylaminopiperidino-substituent with 4-hydroxypiperidino resulted in a series of compounds, which showed in vitro activity with EC50 values in the low nanomolar range, and favourable kinetic properties, such as 40% oral bioavailability. The most promising compound was also tested in a swine in vivo model, resulting in a growth hormone level with a Cmax of over 40 ng mL-1.

Synthetic studies towards proline amide isosteres, potentially useful molecules for biological investigations

2-Ethenylpyrrolidine derivative 8b was prepared from N-protected proline ethyl ester 6b. Bromofluorination of 8b wth NBS-Bu4NF/2HF gave a 1:1 regioisomeric mixture, 9b and 10b (X = Br). Dehydrobromination of 9b and 10b with t-BuOK produced a fluoroolefin 11 and a proline amide isostere model 12, respectively. Deprotection of the Z group in 12 was attempted by treatment with CF3COOH. Although formation of the useful molecule is pseudopeptide synthesis, 13, was observed as checked by NMR spectra, it seemed to decompose slowly during purification procedure to give a mixture of fluorine-free compounds.

Highly Chemoselective Reduction of N-Boc Protected Lactams

N-Boc protected lactams can be reduced chemoselectively in the presence of other groups such as esters, nitriles carbamates or double bonds by first reducing the amide carbonyl group into the corresponding hemiaminal using lithium triethylborohydride foll