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Ethyl chloroformate → 5-tert-Butyl 2-ethyl 3-amino-6,6-dimethylpyrrolo[3,4-c]pyrazole-2,5(4H,6H)-dicarboxylate

HRID 2217350
Notes
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Reaction equation

HRID 2217350 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]2[C:7]([CH3:18])([CH3:17])[N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:9][C:3]=12.C(N(CC)C(C)C)(C)C.Cl[C:29]([O:31][CH2:32][CH3:33])=[O:30]>C1COCC1.CCOC(C)=O>[NH2:1][C:2]1[N:6]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:5]=[C:4]2[C:7]([CH3:18])([CH3:17])[N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:9][C:3]=12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 178451523HCID 178451523, compound

Product 1

HCID 575232455-tert-Butyl 2-ethyl 3-amino-6,6-dimethylpyrrolo[3,4-c]pyrazole-2,5(4H,6H)-dicarboxylateYield 38%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

15 g of tert-Butyl 3-amino-6,6-dimethyl-2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate (59.4 mmol) were dissolved in anhydrous THF (150 ml) and treated, at 0° C. under Ar atmosphere, first with N,N-diisopropylethylamine (50 ml) and then with ClCO2Et (4.65 ml, 1 eq.) dropwise. 90 minutes later, the solvent was diluted with EtOAc (1 l), washed with water and then with brine, dried over sodium sulfate and evaporated. The crude product was purified by flash chromatography (hexane/EtOAc 2/8) to afford 7.3 g of 5-tert-butyl 2-ethyl 3-amino-6,6-dimethylpyrrolo[3,4-c]pyrazole-2,5(4H,6H)-dicarboxylate as the major compound in 38% yield, together with 5.7 g of 5-tert-butyl 1-ethyl 3-amino-6,6-dimethyl-4,6-dihydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate in 30% yield.

Workup

  1. washwashed with water
  2. dry with materialwith brine, dried over sodium sulfate
  3. customevaporated
  4. customThe crude product was purified by flash chromatography (hexane/EtOAc 2/8)

Sources & evidence

ORD record
ord-4eb99bbfcfb440e191b0149f7b21bf1c
Source dataset
uspto-grants-2008_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07407971B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes