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

HRID 1927006Notes

Reaction equation

HRID 1927006 reaction equation
[NH2:1][C:2]1[C:3]2[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:12]([CH3:23])([CH3:22])[C:4]=2[N:5](C(OCC)=O)[N:6]=1.[Li+].[OH-]>CO.CCOC(C)=O>[NH2:1][C:2]1[C:3]2[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:12]([CH3:23])([CH3:22])[C:4]=2[NH:5][N:6]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 573530855-tert-Butyl 1-ethyl 3-amino-6,6-dimethyl-4,6-dihydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a slurry of 5-tert-butyl 1-ethyl 3-amino-6,6-dimethyl-4,6-dihydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate (25.00 g, 77.1 mmol) in MeOH (50 mL) was added LiOH (1.92 g, 77.1 mmol). The reaction was stirred at room temperature for 2 h then concentrated. The crude reaction mixture was taken up in EtOAc (50 mL) then washed with NaHCO3 (20 mL) and water (20 mL). The organic layer was dried (MgSO4), filtered and concentrated to give an orange solid which was triturated with ACN then filtered and rinsed with ACN (50 mL) to give the title compound B1(i) as a white solid (14.8 g, 76%). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.40-1.46 (m, 9H), 1.47-1.54 (m, 6H), 4.03-4.17 (m, 2H), 4.95 (br. s., 1H), 11.15 (s, 1H). Mass spectrum: Calcd for C12H21N4O2 (M+H): 253. Found 253.

Workup

  1. concentrationthen concentrated
  2. customThe crude reaction mixture
  3. washthen washed with NaHCO3 (20 mL) and water (20 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an orange solid which
  8. customwas triturated with ACN
  9. filtrationthen filtered
  10. washrinsed with ACN (50 mL)

Sources & evidence

ORD record
ord-2d9cc65fcde34e56bf8bfe872d8f9256
Source dataset
uspto-grants-2012_05
Patent number
US08183255B2

Reaction notes

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