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Sigma-Aldrich

N-Boc-2,5-dihydro-1H-pyrrole

96%

Synonym(s):

tert-Butyl 2,5-dihydro-1H-pyrrole-1-carboxylate

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About This Item

Empirical Formula (Hill Notation):
C9H15NO2
CAS Number:
73286-70-1
Molecular Weight:
169.22
MDL number:
MFCD01863512
UNSPSC Code:
12352100
PubChem Substance ID:
24871381
NACRES:
NA.22

assay

96%

refractive index

n20/D 1.458 (lit.)

bp

208 °C (lit.)

density

0.981 g/mL at 25 °C (lit.)

SMILES string

CC(C)(C)OC(=O)N1CC=CC1

InChI

1S/C9H15NO2/c1-9(2,3)12-8(11)10-6-4-5-7-10/h4-5H,6-7H2,1-3H3

InChI key

YEBDZDMYLQHGGZ-UHFFFAOYSA-N

General description

N-Boc-2,5-dihydro-1H-pyrrole, also known as tert-butyl 2,5-dihydro-1H-pyrrole-1-carboxylate, can be synthesized from N-boc-diallylamine.

Application

N-Boc-2,5-dihydro-1H-pyrrole (tert-Butyl 2,5-dihydro-1H-pyrrole-1-carboxylate) may be used in the preparation of tert-butyl 3-aryl-2,3-dihydro-1H-pyrrole-1-carboxylate.
Used in a synthesis of ß-aryl-GABA analogues by Heck arylation with arenediazonium salts.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

178.0 °F

flash_point_c

81.1 °C

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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A Short and Efficient Synthesis of (S)-1-Boc-2, 5-dihydro-1H-pyrrole-2-carboxylic Acid.
Sturmer R, et al.
Synthesis, 1, 46-48 (2001)
Synthesis of aryl pyrrolizidines from endocyclic enecarbamates. Novel applications of the Heck arylation of 3-pyrrolines using diazonium salts.
de Oca ACBM and Correia CRD.
ARKIVOC (Gainesville, FL, United States), 10, 390-403 (2003)
Ariel L L Garcia et al.
The Journal of organic chemistry, 70(3), 1050-1053 (2005-01-29)
We report herein a new, practical, and economic synthesis of the phosphodiesterase inhibitor Rolipram on a multigram scale as well as the synthesis of new 4-aryl pyrrolidones and beta-aryl-gamma-amino butyric acids (GABA derivatives) employing an efficient Heck-Matsuda arylation of 3-pyrroline

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