Hydrazine → tert-Butyl 2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate

HRID 241560Notes

Reaction equation

HRID 241560 reaction equation
[NH2:1]N.C[N:4](/[CH:6]=[C:7]1/[CH2:8][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][C:11]/1=O)C>C(O)C>[NH:1]1[C:11]2[CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][C:7]=2[CH:6]=[N:4]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 56971730(Z)-tert-butyl 3-((dimethylamino)methylene)-4-oxopyrrolidine-1-carboxylate

Product 1

HCID 7147072tert-Butyl 2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of hydrazine (3 mL) and tert-butyl (3Z)-3-[(dimethylamino)methylene]-4-oxopyrrolidine-1-carboxylate (19.22 g) in ethanol (40 mL) was heated at 85° C. in a sealed tube for 4 h. Solvent was removed under reduced pressure, and the residue was triturated with dichloromethane (160 mL) and ethyl acetate (15 mL). The resulting solid was filtered. The filtrate was concentrated and the resulting solid was triturated again. The combined solids were used in the next step.

Workup

  1. customSolvent was removed under reduced pressure
  2. customthe residue was triturated with dichloromethane (160 mL) and ethyl acetate (15 mL)
  3. filtrationThe resulting solid was filtered
  4. concentrationThe filtrate was concentrated
  5. customthe resulting solid was triturated again

Sources & evidence

ORD record
ord-fd4c7b181d984b04853f1342e9f2316a
Source dataset
uspto-grants-2014_02
Patent number
US08653059B2

Reaction notes

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