578741-10-3

Basic information

• Product Name: 1-Pyrrolidinecarboxylic acid, 2-(methoxymethyl)-, 1,1-dimethylethyl ester, (2R)-
• CAS NO: 578741-10-3
• Molecular Formula: C11H21NO3
• Mol File: 578741-10-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-Pyrrolidinecarboxylic acid, 2-(methoxymethyl)-, 1,1-dimethylethyl ester, (2R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pyrrolidinecarboxylic acid, 2-(methoxymethyl)-, 1,1-dimethylethyl ester, (2R)-(578741-10-3)
• EPA Substance Registry System: 1-Pyrrolidinecarboxylic acid, 2-(methoxymethyl)-, 1,1-dimethylethyl ester, (2R)-(578741-10-3)

Safety Data

• Hazardous Substances Data: 578741-10-3(Hazardous Substances Data)

Usage

Physical form

Colorless to pale yellow liquid.

Molecular weight

213.3 g/mol.

Solubility

Soluble in organic solvents such as methanol, acetone, and dichloromethane, and is not soluble in water.

Use

Commonly used as an intermediate in the synthesis of pharmaceutical drugs and agrochemicals.

Chemical properties and reactivity

Has potential applications in the pharmaceutical and agricultural industries.

Upstream product

• 15761-39-4 N-tert-butoxycarbonyl-proline 
• 73323-65-6 1-(tert-butyl) 2-methyl (R)-pyrrolidine-1,2-dicarboxylate 
• 145681-01-2 (+/-)-N-tert-butoxycarbonylproline methyl ester 
• 59378-81-3 1-(tert-butoxycarbonyl)prolin-2R-ol 
• 74-88-4 methyl iodide 

Downstream Products

• 578741-08-9 (R)-(+)-1-carbamoyl-2-methoxymethylpyrrolidine 

Relevant articles and documents

Enzyme-catalyzed enantiomeric resolution of N-Boc-proline as the key-step in an expeditious route towards RAMP

For the preparation of both enantiomers of N-carbamoyl-2-methoxymethylpyrrolidine, the precursors of Enders' chiral auxiliaries, SAMP and RAMP, enzyme-catalyzed kinetic resolution of racemic N-carbamoyl, N-Boc, N-Cbz proline esters and prolinols were examined. B. licheniformis protease (subtilisin) preferentially hydrolyzed the (R)-carbamoylproline ester with an enantiomeric ratio (E) of 10. To a hydrophobic N-Cbz proline ester, subtilisin showed lower selectivity (E=2.8), and in contrast, a purified protease (isozyme A) from the earthworm showed the preference of (S)-enantiomer (E=13.6). In a practical sense, C. antarctica lipase B (Chirazyme L-2) was effective for the hydrolysis of both N-Boc and N-Cbz derivatives with E >100. The e.e. of (R)-N-carbamoyl-2-methoxymethylpyrrolidine was raised to be >99.9% by recrystallization at the N-Boc-prolinol stage, which was derived from the (R)-N-Boc-proline methyl ester (98.7% e.e.) through a preparative-scale enzyme-catalyzed resolution (49% yield) of the racemic substrate.