(S)-1-Boc-3-(aminomethyl)pyrrolidine Chemical Properties

Boiling point:

280.3±13.0 °C(Predicted)

Density 

1.044±0.06 g/cm3(Predicted)

refractive index 

1.4780

storage temp. 

2-8°C

pka

10.12±0.29(Predicted)

form 

Liquid

color 

Colorless to yellow

optical activity

Consistent with structure

Sensitive 

Air Sensitive

CAS DataBase Reference

199175-10-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36

Safety Statements 

26

WGK Germany 

3

TSCA 

No

HS Code 

2933998090

(S)-1-Boc-3-(aminomethyl)pyrrolidine Usage And Synthesis

Uses

(S)-1-Boc-3-(Aminomethyl)pyrrolidine is a useful research chemical for organic synthesis and other chemical processes.It is used in preparation of isoquinoline derivatives as progranulin modulators useful in treatment of progranulin- associated disorders.

Synthesis

c) Synthesis of 1,1-dimethylethyl (3S)-3-(aminomethyl)-1-pyrrolidine carboxylate 1,1-Dimethylethyl (3R)-3-cyano-1-pyrrolidine carboxylate (73.9 mmol) was dissolved in ethanol (100 mL) in a Parr bottle. Raney Nickel (73.9 mmol; about 2 scoops of aqueous Raney Nickel) was added under nitrogen protection. After sufficiently displacing the air in the reaction system with nitrogen, the reaction mixture was placed on a Parr shaker at 60 psi hydrogen pressure overnight. Upon completion of the reaction, the reaction mixture was filtered through diatomaceous earth under nitrogen protection and the filter cake was washed with a small amount of ethanol. Subsequently, the filter cake was immediately treated with water. The ethanol filtrate was concentrated under reduced pressure to give the title product as a clear oil (71.9 mmol, 97% yield). The enantiomeric ratio of the product was determined to be 95:5 (i.e. >90% ee). The product was analyzed by chiral HPLC (Daicel Chiralpak AD-H column, 4.6 x 150 mm; mobile phase: heptane:ethanol:isopropylamine=85:10:0.1; flow rate: 1.0 mL/min; UV detection wavelength: 215 nm), and the retention of 1,1-dimethylethyl (3R)-3-(aminomethyl)-1-pyrrolidinecarboxylate time was 4.4 min, and the retention time of 1,1-dimethylethyl (3S)-3-(aminomethyl)-1-pyrrolidine carboxylate was 4.8 min. 1H NMR (400 MHz, CDCl3) δ ppm: 1.47 (s, 9H), 1.54-1.73 (m, 1H), 1.91-2.13 (m, 1H), 2.28-2.52 (m, 1H), 2.78-2.93 (m, 1H), 2.95-3.16 (m, 1H), 3.24-3.67 (m, 5H) .

References

[1] Patent: WO2011/56635, 2011, A1. Location in patent: Page/Page column 50
[2] Patent: WO2011/66211, 2011, A1. Location in patent: Page/Page column 35-36
[3] Patent: WO2013/28445, 2013, A1. Location in patent: Page/Page column 51; 52
[4] Patent: WO2012/37298, 2012, A1. Location in patent: Page/Page column 83

(S)-1-Boc-3-(aminomethyl)pyrrolidine(199175-10-5)Related Product Information

• (S)-1-BOC-3-Cyanopyrrolidine
• (S)-1-Boc-3-(Cbz-amino)-piperidine
• tert-Butanol
• N-Methyl-2-pyrrolidone
• Pyrrolidine
• 1-Methylpyrrolidine
• 2,5-Dimethylpyrrolidine
• Hexamethyldisilazane
• METHYL-2-PYRROLIDONE
• 3-Boc-aminomethylpyrrolidine
• (R)-2-(Aminomethyl)-1-N-Boc-pyyrolidine
• (S)-1-N-Boc-2-(aminomethyl)pyrrolidine
• 2-(Aminomethyl)-1-N-Boc-pyrrolidine
• (R)-1-Boc-3-(aminomethyl)pyrrolidine
• (R)-N-Boc-3-(aminomethyl)pyrrolidine
• (S)-1-Boc-3-(aminomethyl)pyrrolidine