110529-22-1

Basic information

• Product Name: (S)-(+)-2-[HYDROXY(DIPHENYL)METHYL]-1-METHYLPYRROLIDINE
• Synonyms: (S)-(+)-2-[HYDROXY(DIPHENYL)METHYL]-1-METHYLPYRROLIDINE;(S)-N-Methyl-alpha,alpha-diphenylpyrrolidinemethanol;Hydroxydiphenylmethylmethylpyrrolidine;a,a-Diphenyl-N-methyl-L-prolinol;(s)-n-methyl-à,à-diphenylpyrrolidinemethanol;(s)-α,α-diphenyl-n-methyl-2-pyrrolidinemethanol;à,à-diphenyl-n-methyl-l-prolinol;α,α-diphenyl-n-methyl-l-prolinol
• CAS NO: 110529-22-1
• Molecular Formula: C₁₈H₂₁NO
• Molecular Weight: 267.37
• EINECS: -0
• Product Categories: Asymmetric Synthesis;Synthetic Organic Chemistry
• Mol File: 110529-22-1.mol
• Article Data: 11

Chemical Properties

• Melting Point: 66-72 °C
• Boiling Point: 406.8 °C at 760 mmHg
• Flash Point: 196.8 °C
• Appearance: white to pale-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: 4749387
• CAS DataBase Reference: (S)-(+)-2-[HYDROXY(DIPHENYL)METHYL]-1-METHYLPYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-2-[HYDROXY(DIPHENYL)METHYL]-1-METHYLPYRROLIDINE(110529-22-1)
• EPA Substance Registry System: (S)-(+)-2-[HYDROXY(DIPHENYL)METHYL]-1-METHYLPYRROLIDINE(110529-22-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10-34
• Hazardous Substances Data: 110529-22-1(Hazardous Substances Data)

Usage

Reactions

Catalyst for the enantioselective addition of diethylzinc to α,β-unsaturated aldehydes

Chemical Properties

white to slightly yellow 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-/m0/s1

Upstream product

• 113557-12-3 benzyl (S)-(-)-2-(hydroxy(diphenyl)methyl)-1-pyrrolidine carboxylate 
• 50-00-0 formaldehyd 
• 22348-32-9 (S)-diphenylprolinol 
• 152326-82-4 ethyl (S)-(-)-2--1-pyrrolidinecarboxylate 
• 5211-23-4 N-carbobenzyloxy-L-proline methyl ester 
• 77581-28-3 (S)-proline-N-ethyl carbamate methyl ester 
• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 
• 147-85-3 L-proline 
• 100-58-3 phenylmagnesium bromide 
• 137496-68-5 2-[hydroxy(diphenyl)methyl]pyrrolidine-1-carboxylic acid tert-butyl ester 
• 100-59-4 phenylmagnesium chloride 

Downstream Products

• 125183-65-5 (+)-(S)-Diphenyl(1-methylpyrrolidin-2-yl)methyl methacrylate 
• 1042143-98-5 N-methyl-1,1-diphenylpyrrolidinomethanol triflimide salt 

Relevant articles and documents

Asymmetric Sulfinylations of N-Methylephedrine-Modified Tri- or Tetraalkyl Zincates by Symmetric Diaryl Sulfoxides

Diethylzinc was treated with 1 or 2 equiv. of AlkMgCl or PhMgBr (preferably) or with 1 equiv. of nBuLi (less efficiently) for forming species – plausibly zincates – which were sulfinylated by diaryl sulfoxides to give racemic alkyl aryl sulfoxides in yields reaching 100 %. Dialkylzinc reagents were also activated by treatments with 1 or 2 equiv. of an enantiomerically pure alkylmagnesium β-aminoalkoxide. This worked best when the alkoxide stemmed from a dialkylmagnesium reagent and an equimolar amount of N-methyl-(–)-ephedrine. This second activation mode allowed sulfinylations of what was originally the dialkylzinc reagent with diaryl sulfoxides. This generated alkyl aryl sulfoxides with enantiomeric ratios up to 93:7 in up to 100 % yield.

Acceleration of arylzinc formation and its enantioselective addition to aldehydes by microwave irradiation and aziridine-2-methanol catalysts

(Chemical Equation Presented) The formation and 2-amino alcohol catalyzed addition of arylzinc reagents from and with boronic acids, respectively, is drastically accelerated to a few minutes under microwave irradiation without loss of enantioselectivity (up to 98% ee). Of the amino acid derived catalysts tested, the conformationally restricted bulky substituted aziridine-2-methanols derived from serine show the best overall performance in the formation of diarylmethanols.

Catalytic enantioselective aryl transfer: Asymmetric addition of boronic acids to aldehydes using pyrrolidinylmethanols as ligands

Pyrrolidinylmethanols, easily accessible from readily available (S)-proline, were applied in zinc-catalyzed addition of arylboronic acids to aromatic aldehydes; the reaction was found to proceed in excellent yields and high enantioselectivities (up to 98% ee).