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(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol

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CAS:112068-01-6
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(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol Basic information
Product Name:(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol
Synonyms:A,A-DIPHENYL-L-PROLINOL;(s)-(-)-à,à-diphenyl-2-pyrrolidinemethanol;(s)-(-)-à,à-diphenylprolinol;α,α-diphenyl-l-prolinol;2,2-DIPHENYL-(2S)-2-PYRROLIDINEMETHANOL;(S)-(-)-alpha,alpha-diphenyl-2-pyrrolidine;(S)-(-)-ALPHA ALPHA-DIPHENYL-2- PYRROLIDINEMETHANOL 99%;2-PYRROLIDINEMETHANOL, .ALPHA.,.ALPHA.-DIPHENYL-, (2S)-
CAS:112068-01-6
MF:C17H19NO
MW:253.34
EINECS:601-153-1
Product Categories:Peptide;Asymmetric Synthesis;Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry;CHIRAL CHEMICALS;Chiral chemicals;Pharmaceutical intermediate;Chiral Nitrogen;Benzenes;Chiral Reagent;Chiral Reagents;chiral
Mol File:112068-01-6.mol
(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol Structure
(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol Chemical Properties
Melting point 77-80 °C(lit.)
alpha -59 º (c=3, methanol 25 ºC)
Boiling point 396.54°C (rough estimate)
density 1.0078 (rough estimate)
refractive index -66.5 ° (C=3, CHCl3)
storage temp. Inert atmosphere,Room Temperature
solubility Soluble in chloroform.
form powder
pka13.15±0.29(Predicted)
color white to off white ., crystal
optical activity[α]20/D 67°, c = 3 in chloroform
Merck 14,155
BRN 17103
InChIKeyOGCGXUGBDJGFFY-INIZCTEOSA-N
CAS DataBase Reference112068-01-6(CAS DataBase Reference)
NIST Chemistry ReferenceS-(-)-1,1-diphenylprolinol(112068-01-6)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-37/39-24/25-36
WGK Germany 3
10-34
TSCA No
HS Code 29339900
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol Usage And Synthesis
Chemical Propertieswhite to beige crystals or crystalline powder
Usessuzuki reaction
Uses(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol is used to prepare the corresponding oxazaborolidines for the borane-mediated asymmetric reduction of ketones.
PreparationInto a four-necked flask, add tetrahydrofuran, L-proline methyl ester hydrochloride, and phenyl magnesium chloride (dissolved in tetrahydrofuran) solution was added dropwise from a constant pressure dropping funnel, and the addition was completed in about 4 hours, and then stirred at 10-15°C for 3 hours. Add water, adjust the pH to 5-6 with 10% ammonium chloride aqueous solution, extract with dichloromethane, extract the aqueous layer twice with dichloromethane each time, and obtain the organic phase. Wash once with saturated sodium chloride aqueous solution. The organic phase was dried with anhydrous sodium sulfate for 4 hours and filtered. The obtained organic phase was distilled under reduced pressure to distill dichloromethane and tetrahydrofuran to obtain light yellow oily (S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol, yield 86.6%.
(S)-( )-α,α-Diphenyl-2-pyrrolidinemethanol
Application(S)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol (DPPM) may be used in the following processes:
  • DPPM reacts with catecholborane to form a spiroborate ester, which can be an efficient catalyst for the synthesis of enantiopure alcohols by borane reduction of acetophenone.
  • The catalyst generated in situ by reacting DPPM with borane-diethylaniline, can efficiently catalyze the enantioselective reduction of 2′-fluoroacetophenone.
  • Mesoporous SBA-15 silica functionalized with DPPM can catalyze the addition of diethylzinc to benzaldehyde to form (S)-1-phenyl-propanol.
Used to prepare the corresponding oxazaborolidines for the borane-mediated asymmetric reduction of ketones.
General Description(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol is a bifunctional organocatalyst.
(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol Preparation Products And Raw materials
Raw materialsTetrahydrofuran-->Ethyl formate-->L-Proline-->PHENYLMAGNESIUM BROMIDE
Tag:(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol(112068-01-6) Related Product Information
(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol (S)-O-TOLYL-CBS-OXAZABOROLIDINE, 0.5M I& (S)-(-)-ALPHA,ALPHA-DI(2-NAPHTHYL)-2-PYRROLIDINEMETHANOL (S)-(+)-2-[HYDROXY(DIPHENYL)METHYL]-1-METHYLPYRROLIDINE (S)-Tetrahydro-1,3,3-triphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxaborole, 99% (S)-Phenyl oxazaborolidine ALPHA,ALPHA-DIPHENYL-L-PROLINOL METHYLBORONIC ACID CYCL-AMIDE ESTER ALPHA,ALPHA-DIPHENYL-D-PROLINOL METHYLBORONIC ACID CYCL-AMIDE-ESTER ALPHA,ALPHA-DIPHENYL-D-PROLINOL METHYLBORONIC ACID CYCL-AMIDE-ESTER (R)-(+)-a,a-Diphenyl-2-pyrrolidinemethanol L-(+)-Prolinol (S)-ALPHA,ALPHA-BIS(4-FLUOROPHENYL)-2-PYRROLIDINEMETHANOL (S)-(-)N-CARBOMETHOXY-ALPHA,ALPHA-DIPHENYL -2-PYRROLIDINEMETHANOL,98% (S)-ALPHA,ALPHA-BIS(4-METHYLPHENYL)-2-PYRROLIDINEMETHANOL (S)-2-(Methoxydiphenylmethyl)pyrrolidine (S)-ALPHA,ALPHA-BIS(4-METHOXYPHENYL)-2-PYRROLIDINEMETHANOL (2S)-(4,4'-DIISOBUTYLPHENYL)PYRROLIDINE METHANOL SULFATE (S)-(-)-2-[Bis(3,5-dimethylphenyl)hydroxymethyl]pyrrolidine (S,S)-(+)-2,6-BIS[2-(HYDROXYDIPHENYLMETHYL)-1-PYRROLIDINYL-METHYL]-4-METHYLPHENOL