2,6-Dihydro-4H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester Chemical Properties

Boiling point:

366.0±42.0 °C(Predicted)

Density 

1.243±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

14.52±0.20(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C10H15N3O2/c1-10(2,3)15-9(14)13-5-7-4-11-12-8(7)6-13/h4H,5-6H2,1-3H3,(H,11,12)

InChIKey

IBUNCTVDGYIKAP-UHFFFAOYSA-N

SMILES

N1C=C2CN(C(OC(C)(C)C)=O)CC2=N1

2,6-Dihydro-4H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester Usage And Synthesis

Synthesis

The reaction of tert-butyl 3-((dimethylamino)methylene)-4-oxopyrrolidine-1-carboxylate (1 g, 4.16 mmol, 1.00 eq.) with hydrazine hydrate (340 mg, 6.79 mmol, 1.63 eq.) in ethanol (10 mL) was stirred for 5 hours at room temperature. Upon completion of the reaction, the mixture was concentrated under vacuum and the resulting residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether as eluent (gradient elution from 1:5 to 1:2). The final product was 250 mg of tert-butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate in 29% yield as a yellow solid. The product was analyzed by LC/MS (Method C, ESI): retention time RT = 1.30 min, mass spectrum m/z ~ 210.0 [M + H]+.

References

[1] Patent: WO2013/127267, 2013, A1. Location in patent: Page/Page column 97; 98
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 19, p. 5361 - 5366
[3] Patent: EP3144310, 2017, A1