Skip to Content
Merck
All Photos(1)

Documents

427055

Sigma-Aldrich

N-Boc-pyrrolidine

97%

Synonym(s):

tert-Butyl 1-pyrrolidinecarboxylate

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

About This Item

Empirical Formula (Hill Notation):
C9H17NO2
CAS Number:
86953-79-9
Molecular Weight:
171.24
MDL number:
MFCD00216581
UNSPSC Code:
12352100
PubChem Substance ID:
24866734
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.449 (lit.)

bp

80 °C/0.2 mmHg (lit.)

density

0.977 g/mL at 25 °C (lit.)

SMILES string

CC(C)(C)OC(=O)N1CCCC1

InChI

1S/C9H17NO2/c1-9(2,3)12-8(11)10-6-4-5-7-10/h4-7H2,1-3H3

InChI key

LPQZERIRKRYGGM-UHFFFAOYSA-N

Related Categories

General description

N-Boc-pyrrolidine is an N-substituted pyrrolidine. It is reported that the reactivity of N-Boc-pyrrolidine towards C-H insertion reaction is 2000 times more than cyclohexane. It undergoes α-arylation in the presence of a palladium catalyst with high enantioselectivity.

Application

N-Boc-pyrrolidine may be used in the synthesis of the following:
  • 2-aryl-N-boc-pyrrolidines
  • scalemic 2-pyrrolidinylcuprates
  • 2-alkenyl-N-Boc-pyrrolidines
  • 1-deoxycastanospermine
  • methylphenidate analogues
  • (+)-elaeokanine A

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

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

186.8 °F - closed cup

Flash Point(C)

86 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

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

Visit the Document Library

Enantioselective, palladium-catalyzed α-arylation of N-boc-pyrrolidine.
Campos KR, et al.
Journal of the American Chemical Society, 128(11), 3538-3539 (2006)
Copper mediated scalemic organolithium reagents in alkaloid syntheses.
3Dieter RK, et al.
Tetrahedron, 61(13), 3221-3230 (2005)
Synthesis of methylphenidate analogues and their binding affinities at dopamine and serotonin transport sites.
Davies HML, et al.
Bioorganic & Medicinal Chemistry Letters, 14(7), 1799-1802 (2004)
Stereoselective synthesis of hydroxyindolizidines via sparteine-assisted deprotonation of N-Boc-pyrrolidine.
Majewski M, et al.
Tetrahedron Letters, 39(38), 6787-6790 (1998)
Graeme Barker et al.
The Journal of organic chemistry, 76(15), 5936-5953 (2011-07-01)
A comprehensive study of the enantioselective Pd-catalyzed α-arylation of N-Boc pyrrolidine has been carried out. The protocol involves deprotonation of N-Boc pyrrolidine using s-BuLi/(-)-sparteine in TBME or Et(2)O at -78 °C, transmetalation with ZnCl(2) and Negishi coupling using Pd(OAc)(2), t-Bu(3)P-HBF(4)
View All Related Papers

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