Ethyl diazoacetate → Ethyl 5-benzyl-4,6-dioxo-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrazole-3-carboxylate

HRID 341552

Reaction equation

HRID 341552 reaction equation
[N+:1](=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[N-:2].[CH2:9]([N:16]1[C:20](=[O:21])[CH:19]=[CH:18][C:17]1=[O:22])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(OCC)C>[CH2:9]([N:16]1[C:20](=[O:21])[CH:19]2[CH:18]([NH:2][N:1]=[C:3]2[C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:17]1=[O:22])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 12192Ethyl diazoacetateHCID 74204Benzylmaleimide

Product 1

HCID 2857138Ethyl 5-benzyl-4,6-dioxo-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrazole-3-carboxylateYield 90.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl diazoacetate (30.3 mL, 288.5 mmol) was added dropwise over a period of 30 min to a solution of N-benzylmaleimide (49.5 g, 264.7 mmol) in diethyl ether (300 mL) and the mixture was stirred for 4 days at room temperature. The resulting precipitate was filtered off, washed with diethyl ether (100 mL) and dried under vacuum to provide title compound as a white solid (72 g, 90%). Method B HPLC-MS: MH+ requires m/z=302. Found: m/z=302, Rt=1.74 min (83%).

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. washwashed with diethyl ether (100 mL)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-7b1aa99bb42449e88c843b35d03da971
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Linked notes

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