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

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

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

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.

Organocatalytic Nitroaldol Reaction Associated with Deuterium-Labeling

A deuterium-labeling reaction of nitroalkanes in deuterium oxide and the subsequent nitroaldol reaction have been accomplished under basic and organocatalytic conditions to provide the deuterium-labeled β-nitroalcohols in high yields and high deuterium contents. β-Deuterated β-nitroalcohols could be smoothly obtained from the reaction of nitroalkanes and various electrophiles using the easily-removal basic resin WA30. Furthermore, the asymmetric nitroaldol reaction using nitromethane and α-keto esters as electrophiles in the presence of a quinine-derived organocatalyst in deuterium oxide could provide the desired β-deuterated nitroalcohol derivatives with high enantioselectivities. (Figure presented.).

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).

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.

An L-proline-based β-amino tertiary thiol: Synthesis and use as a catalyst in the enantioselective addition of diethylzinc to aldehydes

Two independent routes for the synthesis of the novel β-amino tertiary thiol 1 have been developed. Utilisation of this thiol in the enantioselective addition of diethylzinc to aldehydes provided (R)-secondary alcohols in ees of up to 64%.

Changes of enantioselectivity with the substrate ratio for the addition of diethylzinc to aldehydes using a catalyst coupled to a soluble polymer

α,α-Diphenyl-L-prolinol, when coupled to a polymer soluble in organic solvents, gives surprising results for the addition of diethylzinc to aldehydes.For benzaldehyde, the enantiomeric excess strongly depends on the initial substrate ratio: an excess of d

Catalytic Asymmetric Induction. Highly Enantioselective Addition of Dialkylzincs to Aldehydes Using Chiral Pyrrolidinylmethanols and Their Metal Salts

A series of chiral pyrrolidinylmethanols were synthesized from (S)-proline.Optically active secondary alcohols (R and S enantiomers, respectively) in up to 100percent enantiomeric excess (ee) were obtained in high yields from the enantioselective addition of dialkylzincs to aldehydes catalyzed by 2-5 mol percent of chiral pyrrolidinylmethanols.The sense of the asymmetric induction and the degrees of enantioselectivities were highly dependent on the structure of the catalysts. (+)-DPMPM (3, tertiary amino tertiary alcohol) catalyzed the reaction of aryl, α,β-unsaturated, and aliphatic aldehydes to afford (S) alcohols in high ee's.When the lithium salt of 3 was employed as catalyst in the reactions of aryl and α,β-unsaturated aldehydes, the ee's of (S) alcohols reached 100percent.On the other hand, (-)-erythro-PNPM (10, tertiary amino secondary alcohol) afforded (R) alcohols in high ee (100percent ee).The steric course of the reaction is discussed.