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Sigma-Aldrich

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

99%

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Synonym(s):
(S)-(−)-2-(Diphenylhydroxymethyl)pyrrolidine, α,α-Diphenyl-L-prolinol
Empirical Formula (Hill Notation):
C17H19NO
CAS Number:
112068-01-6
Molecular Weight:
253.34
MDL number:
MFCD00075506
UNSPSC Code:
12352005
PubChem Substance ID:
24862899
NACRES:
NA.22

Quality Level

200

Assay

99%

form

solid

optical activity

[α]20/D −67°, c = 3 in chloroform

mp

77-80 °C (lit.)

SMILES string

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

InChI

1S/C17H19NO/c19-17(16-12-7-13-18-16,14-8-3-1-4-9-14)15-10-5-2-6-11-15/h1-6,8-11,16,18-19H,7,12-13H2/t16-/m0/s1

InChI key

OGCGXUGBDJGFFY-INIZCTEOSA-N

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General description

(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol is a bifunctional organocatalyst.

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Nanoporous silica-supported organocatalyst: a heterogeneous and green hybrid catalyst for organic transformations.
Rostamnia S and Doustkhah E.
Royal Society of Chemistry Advances, 4(54), 28238-28248 (2014)
Highly enantioselective carbonyl reduction with borane catalyzed by chiral spiroborate esters derived from chiral 1, 2-aminoalcohols.
Stepanenko V, et al.
Tetrahedron Asymmetry, 17(1), 112-115 (2006)
Synlett, 929-929 (1993)
Alessandra Lattanzi
Organic letters, 7(13), 2579-2582 (2005-06-17)
[reaction: see text] An operationally simple and mild protocol for the catalytic enantioselective epoxidation of alpha,beta-unsaturated ketones has been estabilished using commercially available alpha,alpha-diphenyl-l-prolinol as bifunctional organocatalyst and tert-butyl hydroperoxide (TBHP) as oxidant. The epoxides have been obtained in good
The enantioselective reduction of 2'-fluoroacetophenone utilizing a simplified CBS-reduction procedure.
Garrett CE, et al.
Tetrahedron Asymmetry, 13(13), 1347-1349 (2002)

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