Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

52927

Sigma-Aldrich

(S)-3-(Boc-amino)pyrrolidine

≥98.0% (TLC)

Synonym(s):

tert-Butyl (S)-3-pyrrolidinylcarbamate

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C9H18N2O2
CAS Number:
122536-76-9
Molecular Weight:
186.25
Beilstein/REAXYS Number:
5377813
MDL number:
MFCD00143194
UNSPSC Code:
12352005
PubChem Substance ID:
57651390
NACRES:
NA.22

assay

≥98.0% (TLC)

form

solid

optical activity

[α]/D -21.5±2.0°, c = 1 in ethanol

SMILES string

CC(C)(C)OC(=O)N[C@H]1CCNC1

InChI

1S/C9H18N2O2/c1-9(2,3)13-8(12)11-7-4-5-10-6-7/h7,10H,4-6H2,1-3H3,(H,11,12)/t7-/m0/s1

InChI key

DQQJBEAXSOOCPG-ZETCQYMHSA-N

Application

(S)-3-(Boc-amino)pyrrolidine can be used as a building block to prepare:
  • 2,4,6-trisubstitued pyrido[3,4-d]pyrimidine derivatives as potent inhibitors against EGFR tyrosine kinase.
  • Aminopyrrolidine scaffolds for asymmetric Morita−Baylis-Hillman reaction.
  • N-benzyl-3-sulfonamidopyrrolidines as potent bacterial cell division inhibitors.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCBZ1833
BCBN6810V
BCBN4504V
BCBM6216V
BCBH7059V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

N-Benzyl-3-sulfonamidopyrrolidines as novel inhibitors of cell division in E. coli
Mukherjee S, et al.
Bioorganic & medicinal chemistry letters, 17(23), 6651-6655 (2007)
Chiral 3-aminopyrrolidines as a rigid diamino scaffold for organocatalysis and organometallic chemistry
Pouliquen M, et al.
Tetrahedron Asymmetry, 21(11-12), 1511-1521 (2010)
Synthesis and biological evaluation of irreversible EGFR tyrosine kinase inhibitors containing pyrido [3, 4-d] pyrimidine scaffold
Zhang H, et al.
Bioorganic & Medicinal Chemistry, 26(12), 3619-3633 (2018)

Articles

MRT - Mono-Boc-Protection of Diamines

Mono-Boc-protected diamines are versatile building blocks for chemical synthesis. Their production is a lot more challenging than the simple reaction scheme might imply, because the Boc-anhydride reagent cannot differentiate between the two identical amino moieties in the substrate.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service