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671193

Sigma-Aldrich

(2S)-N-[(1S,2S)-2-Hydroxy-1,2-diphenylethyl]-2-pyrrolidinecarboxamide

≥99% (HPLC)

Synonym(s):

(2S,1′S, 2′S)-Pyrrolidine-2-carboxylic acid (2-hydroxy-1,2-diphenyl-ethyl)amide

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About This Item

Empirical Formula (Hill Notation):
C19H22N2O2
CAS Number:
529486-26-8
Molecular Weight:
310.39
MDL number:
MFCD10000880
UNSPSC Code:
12352005
PubChem Substance ID:
329760409
NACRES:
NA.22

Assay

≥99% (HPLC)

optical activity

[α]/D -25±2°, c = 2 in ethanol

mp

127-131 °C

storage temp.

2-8°C

SMILES string

O[C@H]([C@@H](NC(=O)[C@@H]1CCCN1)c2ccccc2)c3ccccc3

InChI

1S/C19H22N2O2/c22-18(15-10-5-2-6-11-15)17(14-8-3-1-4-9-14)21-19(23)16-12-7-13-20-16/h1-6,8-11,16-18,20,22H,7,12-13H2,(H,21,23)/t16-,17-,18-/m0/s1

InChI key

JVOUIFUIIPEWLM-BZSNNMDCSA-N

Application

(2S)-N-[(1S,2S)-2-Hydroxy-1,2-diphenylethyl]-2-pyrrolidinecarboxamide can be used as a catalyst:
  • In the synthesis of α-hydroxyamino carbonyl compounds by reacting aldehydes with nitrosobenzenes via N-nitroso aldol reaction.[1]
  • In the direct aldol reactions of aldehydes with chloroacetones[2], methylthio- and fluoroacetones.[3]

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

Signal Word

Danger

Hazard Statements

H301 + H331,H410

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
1394174V
1394174
1331851

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L-Prolinamide-catalyzed direct nitroso aldol reactions of α-branched aldehydes: A distinct regioselectivity from that with L-proline
Guo H, et al.
Chemical Communications (Cambridge, England), 429-431 (2006)
l-Proline amides catalyze direct asymmetric aldol reactions of aldehydes with methylthioacetone and fluoroacetone
Xu X, et al.
Tetrahedron Asymmetry, 18(2), 237-242 (2007)
L-Proline amide-catalyzed direct asymmetric aldol reaction of aldehydes with chloroacetone
He L, et al.
Tetrahedron, 62(2-3), 346-351 (2006)

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