3-N-Boc-aminopyrrolidine

3-N-Boc-aminopyrrolidine Property

Melting point:

67 °C

Boiling point:

286.4±29.0 °C(Predicted)

Density 

1.04±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Soluble in Methanol(almost transparency).

pka

12.37±0.20(Predicted)

form 

powder to crystal

color 

White to Light yellow to Light orange

Sensitive 

Air Sensitive

InChIKey

DQQJBEAXSOOCPG-UHFFFAOYSA-N

CAS DataBase Reference

99724-19-3(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3-N-Boc-aminopyrrolidine Chemical Properties,Usage,Production

Uses

(+/-)-3-(Boc-amino)pyrrolidine is the homochiral starting materials utilised in the synthesis of all of the chiral compounds. Reactant in the peptide activated G-protein coupled receptors test.

Synthesis

General procedure for the synthesis of 3-(Boc-amino)pyrrolidine from 1-benzyl-3-(Boc-amino)pyrrolidine: 1-benzyl-3-(Boc-amino)pyrrolidine (15.75 g, 57.0 mmol) was dissolved in a solvent mixture of methanol and tetrahydrofuran (4:1, 114 ml) in a 500 ml reaction vessel. A catalytic amount of 10% palladium/carbon (Pd/C) was added to the solution. The reaction mixture was stirred and reacted for 12 hours under hydrogen atmosphere. Upon completion of the reaction, the palladium/carbon catalyst was removed by filtration through a diatomaceous earth pad and the filtrate was concentrated under reduced pressure to remove the solvent. The resulting residue was purified by silica gel column chromatography to afford 3-(Boc-amino)pyrrolidine (9.51 g, 99% yield). The product was characterized by 1H-NMR (200 MHz, CDCl3): δ 1.41 (s, 9H), 2.26 (m, 2H), 2.55 (m, 3H), 2.74 (m, 1H), 4.84 (br, 1H).LC-MS analysis showed [M+H]+ peak of 187.

References

[1] Patent: WO2008/54154, 2008, A1. Location in patent: Page/Page column 76; 81; 162-163; 168
[2] Patent: WO2007/52938, 2007, A1. Location in patent: Page/Page column 23
[3] Patent: US5281612, 1994, A
[4] Patent: US4604401, 1986, A
[5] Patent: US4617308, 1986, A