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670197

Sigma-Aldrich

(S)-2-(Methoxydiphenylmethyl)pyrrolidine

95% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C18H21NO
CAS Number:
118971-03-2
Molecular Weight:
267.37
MDL number:
MFCD09750440
UNSPSC Code:
12352005
PubChem Substance ID:
24885069
NACRES:
NA.22

Assay

95% (HPLC)

optical purity

ee: ≥99.5% (HPLC)

storage temp.

2-8°C

SMILES string

COC([C@@H]1CCCN1)(c2ccccc2)c3ccccc3

InChI

1S/C18H21NO/c1-20-18(17-13-8-14-19-17,15-9-4-2-5-10-15)16-11-6-3-7-12-16/h2-7,9-12,17,19H,8,13-14H2,1H3/t17-/m0/s1

InChI key

CGUGCZSRPDCLBT-KRWDZBQOSA-N

Application

(S)-2-(Methoxydiphenylmethyl)pyrrolidine is a diphenylprolinol methyl ether, which can be used as a catalyst to synthesize:
  • Enantioselective ketones via intermolecular asymmetric Michael addition of aldehydes to nonactivated enones.
  • Stereoselective chiral bipyrazolidin-3-one derivatives by dipolar cycloaddition reaction of azomethine imines with α, β-unsaturated aldehydes.
  • Enantioenriched spiro nitrogen heterocycles via asymmetric nucleophilic epoxidation of α-ylideneoxindole esters.
  • Optically active secondary alcohols by asymmetric addition of Et2Zn to various aldehydes.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Diphenylprolinol methyl ether: a highly enantioselective catalyst for Michael addition of aldehydes to simple enones
Chi Y and Gellman SH
Organic Letters, 7(19), 4253-4256 (2005)
Noncovalent organocatalysis: A powerful tool for the nucleophilic epoxidation of α-ylideneoxindoles
Palumbo C, et al.
Organic Letters, 13(23), 6248-6251 (2011)
Organocatalytic and Stereoselective [3+ 2] Cycloadditions of Azomethine Imines with , α, β-Unsaturated Aldehydes
Chen W, et al.
Advanced Synthesis & Catalysis, 348(14), 1818-1822 (2006)
Chiral pyrrolidine derivatives as catalysts in the enantioselective addition of diethylzinc to aldehydes
Yang X, et al.
Tetrahedron Asymmetry, 10(1), 133-138 (1999)
Organocatalytic and Stereoselective [3+ 2] Cycloadditions of Azomethine Imines with , α, β-Unsaturated Aldehydes
Chen W, et al.
advanced synthesis and catalysis, 348(14), 1818-1822 (2006)

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