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462403

Sigma-Aldrich

Benzyl (S)-(−)-2-(1-pyrrolidinylcarbonyl)-1-pyrrolidinecarboxylate

97%

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About This Item

Empirical Formula (Hill Notation):
C17H22N2O3
CAS Number:
Molecular Weight:
302.37
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

assay

97%

form

solid

optical activity

[α]24/D −14°, c = 1.6 in methanol

mp

132-135 °C (lit.)

SMILES string

O=C(OCc1ccccc1)N2CCC[C@H]2C(=O)N3CCCC3

InChI

1S/C17H22N2O3/c20-16(18-10-4-5-11-18)15-9-6-12-19(15)17(21)22-13-14-7-2-1-3-8-14/h1-3,7-8,15H,4-6,9-13H2/t15-/m0/s1

InChI key

VJDNUCLKCQKXMM-HNNXBMFYSA-N

Application

Benzyl (S)-(−)-2-(1-pyrrolidinylcarbonyl)-1-pyrrolidinecarboxylate can be used as an intermediate in the preparation of:
  • An organocatalyst, which is used in the Michael addition of cyclic ketones.[1]
  • Hydrazone-based chiral auxiliary, which is used to prepare chiral ketones.[2]

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Investigation of a novel diamine based chiral auxiliary in the asymmetric alkylation of ketones
Clarke SL, et al.
Tetrahedron Asymmetry, 25(4), 356-361 (2014)
A highly enantioselective organocatalyst for the Michael addition of cyclic ketones to nitroolefins
Zhu M, et al.
Tetrahedron Asymmetry, 17(4), 491-493 (2006)

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