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427055

Sigma-Aldrich

N-Boc-pyrrolidine

97%

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Synonym(s):
tert-Butyl 1-pyrrolidinecarboxylate
Empirical Formula (Hill Notation):
C9H17NO2
CAS Number:
Molecular Weight:
171.24
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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This Item
343536425834477516
N-Boc-pyrrolidine 97%

Sigma-Aldrich

427055

N-Boc-pyrrolidine

1-Boc-piperazine 97%

Sigma-Aldrich

343536

1-Boc-piperazine

N-Boc-pyrrole 98%

Sigma-Aldrich

425834

N-Boc-pyrrole

form

liquid

form

solid

form

liquid

form

-

refractive index

n20/D 1.449 (lit.)

refractive index

-

refractive index

n20/D 1.4685 (lit.)

refractive index

n20/D 1.458 (lit.)

bp

80 °C/0.2 mmHg (lit.)

bp

-

bp

91-92 °C/20 mmHg (lit.)

bp

208 °C (lit.)

density

0.977 g/mL at 25 °C (lit.)

density

-

density

1 g/mL at 25 °C (lit.)

density

0.981 g/mL at 25 °C (lit.)

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

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

Signal Word

Warning

Hazard Statements

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

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Stereoselective synthesis of hydroxyindolizidines via sparteine-assisted deprotonation of N-Boc-pyrrolidine.
Majewski M, et al.
Tetrahedron Letters, 39(38), 6787-6790 (1998)
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)
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)
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)

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