13515-74-7

Basic information

• Product Name: methyl 1-tritylprolinate
• CAS NO: 13515-74-7
• Molecular Formula: C₂₅H₂₅NO₂
• Molecular Weight: 371.4715
• Mol File: 13515-74-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 459.5°C at 760 mmHg
• Flash Point: 134.6°C
• Density: 1.151g/cm³
• Vapor Pressure: 1.26E-08mmHg at 25°C
• Refractive Index: 1.6
• CAS DataBase Reference: methyl 1-tritylprolinate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 1-tritylprolinate(13515-74-7)
• EPA Substance Registry System: methyl 1-tritylprolinate(13515-74-7)

Safety Data

• Hazardous Substances Data: 13515-74-7(Hazardous Substances Data)

Usage

General Description

Methyl 1-tritylprolinate is an organic chemical compound that belongs to the class of amino acid derivatives. It is formed by the esterification of the carboxylic acid group of proline with methanol and 1-trityl chloride. methyl 1-tritylprolinate is commonly used as a chiral building block in the synthesis of various pharmaceuticals and biologically active molecules. Methyl 1-tritylprolinate is known for its ability to provide excellent stereochemical control in asymmetric synthesis and has been used in the production of drugs for treating depression, anxiety, and other neurological conditions. Its unique structural and functional properties make it an important intermediate in the pharmaceutical and chemical industries.

Upstream product

• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 76-83-5 trityl chloride 
• 2133-40-6 L-proline methyl ester monohydrochloride 
• 43041-12-9 methyl pyrrolidine-2-carboxylate 
• 67-56-1 methanol 
• 147-85-3 L-proline 

Downstream Products

• 43041-12-9 methyl pyrrolidine-2-carboxylate 
• 1403755-25-8 (S)-2-[(R)-fluoro(phenyl)methyl]pyrrolidine 
• 628292-14-8 (αR,2S)-α-(1-butyl)-1-triphenylmethyl-2-pyrrolidinemethanol 
• 628292-19-3 (αR,2S)-α-phenyl-1-triphenylmethyl-2-pyrrolidinemethanol 
• 628292-20-6 (αR,2S)-α-(2-propenyl)-1-triphenylmethyl-2-pyrrolidinemethanol 
• 628292-16-0 (αR,2S)-α-(1-methylethyl)-1-triphenylmethyl-2-pyrrolidinemethanol 
• 628292-17-1 (αR,2S)-α-ethenyl-1-triphenylmethyl-2-pyrrolidinemethanol 
• 628292-15-9 (αR,2S)-α-methyl-1-triphenylmethyl-2-pyrrolidinemethanol 
• 628292-12-6 (2S)-1-triphenylmethyl-2-pyrrolidinemethanal 
• 110529-23-2 (αR,2S)-1-methyl-α-phenyl-2-pyrrolidinemethanol 
• 74936-95-1 (S)-α-<(R)-pyrrolidin-2-yl>benzyl alcohol 
• 119866-62-5 2-methoxycarbonyl-5-pyrroline 
• 119866-64-7 2-Chloro-3,4-dihydro-2H-pyrrole-2-carboxylic acid methyl ester 
• 119866-63-6 4-Chloro-3,4-dihydro-2H-pyrrole-2-carboxylic acid methyl ester 

Relevant articles and documents

Enantioselective ring expansion of prolinol derivatives. Two formal syntheses of (-)-swainsonine

Two enantioselective formal syntheses of (-)-swainsonine have been achieved from l-proline by using an enantioselective ring enlargement of substituted prolinols as the key step. The more efficient synthesis has been achieved in 14 steps with an overall yield of 14%.

Stereoselective Rearrangement of (Trifluoromethyl)prolinols to Enantioenriched 3-Substituted 2-(Trifluoromethyl)piperidines

3-Substituted 2-(trifluoromethyl)piperidines B were synthesized by ring expansion of (trifluoromethyl)prolinols A, which were obtained from l-proline via an aziridinium intermediate C. The ring opening of the (trifluoromethyl)aziridinium intermediate by different nucleophiles is regio- and diastereoselective.

Ceric ammonium nitrate-mediated detritylation of tritylated amines

Efficient deprotection of tritylated amines to the corresponding amines mediated by 20 mol % ceric ammonium nitrate [Ce(NH4) 2(NO3)6, CAN], 10 equiv of acetic acid and 15 equiv of water in dichloromethane is presented. This method equally worked well in the case of morpholino nucleosides.