Hydrazinium chloride → tert-Butyl 3-amino-6,6-dimethyl-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate

HRID 1479041Notes

Reaction equation

HRID 1479041 reaction equation
Cl.[NH2:2][NH2:3].[C:4]([CH:6]1[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:8]([CH3:19])([CH3:18])[C:7]1=O)#[N:5]>CCO>[NH2:5][C:4]1[C:6]2[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:8]([CH3:19])([CH3:18])[C:7]=2[NH:2][N:3]=1

Participants

4

Reactant 2

HCID 115031Hydrazinium chlorideHCID 42609241Tert-butyl 4-cyano-2,2-dimethyl-3-oxopyrrolidine-1-carboxylate

Product 1

HCID 40152088tert-Butyl 3-amino-6,6-dimethyl-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylateYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

Hydrazine hydrochloride (4.95 g, 72.4 mmol) was added to a solution of tert-butyl 4-cyano-2,2-dimethyl-3-oxopyrrolidine-1-carboxylate (11.5 g, 48.2 mmol) in EtOH (300 mL) and the reaction mixture was stirred at 85° C. for 18 hours then concentrated in vacuo. The residue was taken up in EA (200 mL), washed with sat. aq. NaHCO3, dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography (3% MeOH in EA) afforded the title compound (5.5 g, 46%) as an off-white solid. 1H NMR (DMSO-d6) δ 11.12 (s, 1H), 5.05 (s, 2H), 4.11-4.07 (m, 2H), 1.50-1.48 (m, 6H), 1.44-1.41 (m, 9H).

Workup

  1. concentrationthen concentrated in vacuo
  2. washwashed with sat. aq. NaHCO3
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography (3% MeOH in EA)

Sources & evidence

ORD record
ord-48faea06d9a34698a0391d15564c2923
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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