144119-12-0

Basic information

• Product Name: (R)-alpha,alpha-Diphenylmethylprolinol
• Synonyms: (R)-A,A-DIPHENYLMETHYLPROLINOL;(R)-A,A-DIPHENYL-N-METHYL-2-PYRROLIDINEMETHANOL;(R)-ALPHA,ALPHA-DIPHENYLMETHYLPROLINOL;(R)-ALPHA,ALPHA-DIPHENYL-N-METHYL-2-PYRROLIDINEMETHANOL;(R)-(-)-DIPHENYL(1-METHYLPYRROLIDIN-2-YL)METHANOL;(R)-N-METHYL- ALPHA,ALPHA-DIPHENYL-2-PYRROLIDINE METHANOL;ALPHA,ALPHA-DIPHENYL-N-METHYL-D-PROLINOL;1,1,1-DIPHENYL-(N-METHYL-PYRROLINE-2YL)-METHANOL
• CAS NO: 144119-12-0
• Molecular Formula: C₁₈H₂₁NO
• Molecular Weight: 267.37
• EINECS: -0
• Product Categories: Asymmetric Synthesis;Synthetic Organic Chemistry
• Mol File: 144119-12-0.mol

Chemical Properties

• Melting Point: 68-71 °C
• Boiling Point: 406.791 °C at 760 mmHg
• Flash Point: 196.766 °C
• Appearance: white to light-yellow/Powder
• Density: 1.116 g/cm³
• Vapor Pressure: 2.39E-07mmHg at 25°C
• Refractive Index: -55 ° (C=1, CHCl3)
• Storage Temp.: 0-6°C
• PKA: 13.15±0.29(Predicted)
• BRN: 1535407
• CAS DataBase Reference: (R)-alpha,alpha-Diphenylmethylprolinol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-alpha,alpha-Diphenylmethylprolinol(144119-12-0)
• EPA Substance Registry System: (R)-alpha,alpha-Diphenylmethylprolinol(144119-12-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10-34
• Hazardous Substances Data: 144119-12-0(Hazardous Substances Data)

Usage

Reaction

Chiral amino alcohol assisted asymmetric, enantioselective, aryl transfer of triphenylboroxin to a set of aryl aldehydes in the presence of chiral amino alcohols derived from (S)-proline. Pyrrolidinylmethanol compound used for the zinc-catalyzed addition of arylboronic acids to aromatic aldehydes, proceeding in high yields and high enantioselectivities (up to 98% ee).

Chemical Properties

white to off-white crystalline powder

InChI:InChI=1/C18H21NO/c1-19-14-8-13-17(19)18(20,15-9-4-2-5-10-15)16-11-6-3-7-12-16/h2-7,9-12,17,20H,8,13-14H2,1H3/p+1/t17-/m1/s1

Upstream product

• 185246-66-6 1-ethyl methyl (2R)-pyrrolidine-1,2-dicarboxylate 
• 77-78-1 dimethyl sulfate 
• 112022-83-0 (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole 

Relevant articles and documents

Process for preparing Ezetimibe intermediate by enantioselective CBS catalyzed ketone reduction with BH3-DEA prepared in situ

The (S) alcohol in the benzylic position of compound 2, a key intermediate in the synthesis of the cholesterol lowering agent Ezetimibe, was introduced by the (R)-MeCBS catalyzed asymmetric carbonyl reduction of ketone 1 using borane diethylaniline complex (BDEA) as the reducing agent. The latter was prepared in situ from sodium borohydride (NaBH4), diethylaniline (DEA) and dimethylsulfate (DMSO4). BDEA prepared in situ offers considerable advantages from the industrialization standpoint (cost and stability on storage of the reagents) over commercial solutions of BH3-THF (BTHF) or BH3-DMS (BMS). The effect of critical reaction parameters such as addition mode of reagent, temperature, solvent, reaction quenching as well as LiCl addition on the selectivity has been examined. This reaction has been successfully applied in the process for the preparation of key intermediate 2 for Ezetimibe.

Catalyzed asymmetric aryl transfer reactions to aldehydes with boroxines as aryl source

Asymmetric aryl transfer of triphenylboroxin to a set of aryl aldehydes has been carried out in the presence of chiral amino alcohols derived from (S)-proline with high enantioselectivity. Substituted phenyl boroxins were also used as aryl source in asymmetric arylation of benzaldehyde.