121817-71-8

Usage

Uses

Used in Industrial Synthesis:
(R)-(+)-2-(Methoxymethyl)-1-pyrrolidinecarboxaldehyde is used as an intermediate in the synthesis of complex organic compounds for various industrial applications. Its chemical reactivity and unique structure make it a valuable component in the production of a wide range of products.
Used in Laboratory Research:
In the field of organic chemistry, (R)-(+)-2-(Methoxymethyl)-1-pyrrolidinecarboxaldehyde is used as a research compound to study its properties, reactivity, and potential applications in the development of new materials and compounds.
Used in Production Facilities:
(R)-(+)-2-(METHOXYMETHYL)-1-PYRROLIDINECARBOXALDEHYDE is utilized in specialized production facilities where it serves as a key component in the manufacturing process of various organic compounds, contributing to the final product's properties and performance.
Environmental Considerations:
The persistence and degradability, toxicity, and physical and chemical hazards related to (R)-(+)-2-(Methoxymethyl)-1-pyrrolidinecarboxaldehyde are important factors to consider for its safe handling and environmental implications. Proper management and disposal methods are crucial to minimize potential harm to the environment and human health.

InChI:InChI=1/C7H13NO2/c1-10-5-7-3-2-4-8(7)6-9/h6-7H,2-5H2,1H3/t7-/m1/s1

Upstream product

• 124-38-9 carbon dioxide 
• 63126-47-6 (2R)-methoxymethylpyrrolidine 
• 63126-47-6 (2S)-2-(methoxymethyl)-1-pyrrolidine 
• 147-85-3 L-proline 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 
• 344-25-2 D-Prolin 
• 68832-13-3 D-prolinol 
• 74-88-4 methyl iodide 
• 55456-46-7 (S)-(-)-1-Formyl-2-(hydroxymethyl)pyrrolidine 

Downstream Products

• 73473-33-3 2-<(2S)-2-Methoxymethyl-1-pyrrolidinylmethyleneamino>benzenepropanoic acid, methyl ester 
• 95312-82-6 (S)-(-)-1-carbamoyl-2-methoxymethylpyrrolidine 
• 121817-72-9 (R)-2-(methoxymethyl)pyrrolidine hydrochloride 
• 578741-08-9 (R)-(+)-1-carbamoyl-2-methoxymethylpyrrolidine 

Relevant academic research and scientific papers

Tetracoordinate borates as catalysts for reductive formylation of amines with carbon dioxide

We report sodium trihydroxyaryl borates as the first robust tetracoordinate organoboron catalysts for reductive functionalization of CO2. These catalysts, easily synthesized from condensing boronic acids with metal hydroxides, activate main group element-hydrogen (E-H) bonds efficiently. In contrast to BX3 type boranes, boronic acids and metal-BAr4 salts, under transition metal-free conditions, sodium trihydroxyaryl borates exhibit high reactivity of reductive N-formylation toward a variety of amines (106 examples), including those with functional groups such as ester, olefin, hydroxyl, cyano, nitro, halogen, MeS-, ether groups, etc. The over-performance to catalyze formylation of challenging pyridyl amines affords a promising alternative method to the use of traditional formylation reagents. Mechanistic investigation supports electrostatic interactions as the key for Si/B-H activation, enabling alkali metal borates as versatile catalysts for hydroborylation, hydrosilylation, and reductive formylation/methylation of CO2.

Stereoselective alkylations of chiral nitro imine and nitro hydrazone dianions. Synthesis of enantiomerically enriched 3-substituted 1-nitrocyclohexenes

(Chemical Equation Presented) Dianions of chiral nitro imines (generated by a combination of LDA and s-BuLi) underwent diastereoselective alkylation with methyl, butyl, isopropyl, allyl, and methallyl iodides. In contrast to the behavior of simple metalloenamines, the most selective auxiliary contained no coordinating groups but did possess a large steric difference between the two substituents. The yield and selectivity of the alkylations were improved by the addition of HMPA or DMPU. The use of (S)-1-naphthylethylamine as the auxiliary afforded the R absolute configuration of the alkylation products. This stereochemical outcome could be rationalized by simple steric approach controlled alkylation in a conformationally fixed, internally coordinated dianion. A SAMP nitro hydrazone gave poorer yields and selectivities.

Photochemical and thermal isomerization processes of a chiral auxiliary based donor-acceptor substituted chiroptical molecular switch: Convergent synthesis, improved resolution and switching properties

A new type of chiroptical molecular switch is presented where irradiation employing different wavelengths of light induces a reversible helix inversion of a sterically overcrowded alkene bearing a second chiral entity in the form of a stereogenic center present in a pyrrolidine unit. The additional stereogenic center in the chiral auxiliary group has a distinct influence on the switching selectivity of this system and greatly facilitates the resolution of the different diastereoisomers, which is a considerable improvement compared with previously reported systems. In addition, the pyrrolidine stereogenic center causes small energetic differences between the various states of the switch system resulting in a small but significant directional preference in the helix inversion steps.

Asymmetric Diels-Alder Reactions with Sulfines Derived from Proline

The Synthesis of a variety of sulfines 8 derived from S-proline, utilizing the reaction of α-silyl carbanions with sulfur dioxide, is described.Reaction of the thus prepared sulfines 8 with 2,3-dimethyl-1,3-butadiene gave dihydrothiopyran S-oxides 9.During these cycloaddition reactions asymmetric inductions up to 40percent were observed.From one pure diastereomeric form of cycloadduct 9d an X-ray analysis was carried out in order to provide insight in the steric course of the cycloaddition reaction.