Carbamic acid, [(3R)-3-pyrrolidinylmethyl]-, 1,1-dimethylethyl ester (9CI) Chemical Properties

Boiling point:

303.9±15.0 °C(Predicted)

Density 

0.997±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

12.71±0.46(Predicted)

Appearance

white solid

Carbamic acid, [(3R)-3-pyrrolidinylmethyl]-, 1,1-dimethylethyl ester (9CI) Usage And Synthesis

Uses

(R)-tert-butyl pyrrolidin-3-ylmethylcarbamate is a useful reagent in the research discovery of ethyl 5,6-dihydropyrazolo[1,5-c]quinazoline-1-carboxylate, a catalytic inhibitor of DNA gyrase and a potential antibacterial agent.

Synthesis

General procedure: tert-butyl (R)-(1-benzylpyrrolidin-3-ylmethyl)carbamate (1.00 g, 3.44 mmol) was mixed with 20% Pd/C and subjected to hydrogenation under hydrogen pressure of 50 psi.After 48 h, the reaction mixture was filtered to remove the catalyst, and the filtrate was concentrated to give 511 mg of tert-butyl (3R)-pyrrolidin-3-methylcarbamate ( Yield: 74%). Mass spectrometry analysis (APCI+): m/z 201 ([M + H]+).

References

[1] Patent: WO2005/49602, 2005, A1. Location in patent: Page/Page column 87; 88; 121
[2] Patent: WO2005/49605, 2005, A1. Location in patent: Page/Page column 115; 116; 149

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