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Merck
CN

671304

(R)-α,α-Bis(3,5-dimethylphenyl)-2-pyrrolidinemethanol trimethylsilyl ether hydrochloride

97%

Synonym(s):

(R)-α,α-Bis(3,5-dimethylphenyl)prolinol-trimethylsilyl ether hydrobromide, (R)-2-[Bis(3,5-dimethylphenyl)(trimethylsilyloxy)methyl]pyrrolidine hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C24H35NOSi · HCl
CAS Number:
1217450-13-9
Molecular Weight:
418.09
UNSPSC Code:
12352005
PubChem Substance ID:
329760416
MDL number:
MFCD10566968

Key Documents

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InChI

1S/C24H35NOSi.ClH/c1-17-11-18(2)14-21(13-17)24(26-27(5,6)7,23-9-8-10-25-23)22-15-19(3)12-20(4)16-22;/h11-16,23,25H,8-10H2,1-7H3;1H/t23-;/m1./s1

SMILES string

Cl.Cc1cc(C)cc(c1)C(O[Si](C)(C)C)([C@H]2CCCN2)c3cc(C)cc(C)c3

InChI key

WTDMRDKYLPARGO-GNAFDRTKSA-N

assay

≥96.5% (HPLC), 97%

optical purity

enantiomeric excess: ≥96.5% (HPLC)

mp

159-163 °C

storage temp.

2-8°C

Application

Catalyst for enantioselective ene reaction; dienamine catalysis; catalyst for alpha-sulfenylation of aldehydes

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
1332260V
1332260

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Enantioselective ene reaction of cyclopentadiene and alpha,beta-enals catalyzed by a diphenylprolinol silyl ether.
Hiroaki Gotoh et al.
Angewandte Chemie (International ed. in English), 45(41), 6853-6856 (2006-09-27)
Søren Bertelsen et al.
Journal of the American Chemical Society, 128(39), 12973-12980 (2006-09-28)
A new concept in organocatalysis is presented, the direct asymmetric gamma-functionalization of alpha,beta-unsaturated aldehydes. We disclose that secondary amines can invert the usual reactivity of alpha,beta-unsaturated aldehydes, enabling a direct gamma-amination of the carbonyl compound using azodicarboxylates as the electrophilic
Enantioselective organocatalyzed alpha sulfenylation of aldehydes.
Mauro Marigo et al.
Angewandte Chemie (International ed. in English), 44(5), 794-797 (2005-01-20)

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