3-N-Boc-aminopyrrolidine Chemical Properties

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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

3-N-Boc-aminopyrrolidine Usage And Synthesis

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

3-N-Boc-aminopyrrolidine(99724-19-3)Related Product Information

• tert-Butyl peroxybenzoate
• N-Vinyl-2-pyrrolidone
• tert-Butyl 4-aminobenzoate
• tert-Butyl glycinate
• tert-Butyl carbazate
• Pyrrolidine
• 3-Aminopyrrolidine
• Polyvinylpyrrolidone
• Povidone iodine
• tert-Butyl carbamate
• N-Methyl-2-pyrrolidone
• DI-TERT-BUTYL ETHER
• METHYL-2-PYRROLIDONE
• (4-PHENYLPYRROLIDIN-3-YL)CARBAMIC ACID TERT-BUTYL ESTER
• 3-(N-TERT-BUTOXYCARBONYL-N-METHYLAMINO)PYRROLIDINE
• (S)-3-(Boc-amino)pyrrolidine
• 1-BENZYL-3-(TERT-BUTOXYCARBONYLAMINO)PYRROLIDINE
• t-butyl chloroformate