tert-Butyl 3-(bromomethyl)pyrrolidine-1-carboxylate Chemical Properties

Boiling point:

300.1±15.0 °C(Predicted)

Density 

1.312±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

-2.14±0.40(Predicted)

Appearance

Colorless to light yellow Liquid

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HazardClass 

IRRITANT

HS Code 

2933998090

tert-Butyl 3-(bromomethyl)pyrrolidine-1-carboxylate Usage And Synthesis

Chemical Properties

Liquid

Synthesis

The general procedure for the synthesis of 1-Boc-3-(bromomethyl)pyrrolidine from 1-Boc-3-hydroxymethylpyrrolidine was as follows: 1,1-dimethylethyl-3-(hydroxymethyl)-1-pyrrolidine carboxylate (0.56 g, 2.8 mmol) was dissolved in dichloromethane (10 mL) under the protection of nitrogen and carbon tribromide (1.39 g, 4.2 mmol) was added. Subsequently, a solution of triphenylphosphine (0.73 g, 2.8 mmol) in dichloromethane (5 mL) was added slowly and dropwise. After the dropwise addition, the reaction mixture was stirred at room temperature for 18 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in a 10% ethyl acetate/90% hexane solvent mixture, stirred and filtered. The filtrate was purified by silica gel column chromatography using a gradient elution of 0-25% ethyl acetate/hexane, and the target fraction was collected to give 1-Boc-3-(bromomethyl)pyrrolidine (0.41 g, 55% yield). Mass spectrum (electrospray positive ion mode) m/z 264 ([M+H]+).

References

[1] Patent: WO2007/58850, 2007, A2. Location in patent: Page/Page column 52-53
[2] Journal of Medicinal Chemistry, 2008, vol. 51, # 18, p. 5663 - 5679
[3] Patent: WO2008/121685, 2008, A1. Location in patent: Page/Page column 46
[4] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 5, p. 1151 - 1175

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