Hydrazine hydrate (1:1) → HCID 68864415, compound

HRID 494096Notes

Reaction equation

HRID 494096 reaction equation
[C:1]([C:4]1[N:8]2[CH2:9][CH2:10][N:11]([CH3:14])[C:12](=[O:13])[C:7]2=[C:6]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:5]=1[C:23]([O:25]CC)=O)(=O)[CH3:2].O.[NH2:29][NH2:30]>C(O)(=O)C>[CH2:16]([O:15][C:6]1[C:5]2[C:23](=[O:25])[NH:30][N:29]=[C:1]([CH3:2])[C:4]=2[N:8]2[CH2:9][CH2:10][N:11]([CH3:14])[C:12](=[O:13])[C:7]=12)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68866335Ethyl 6-acetyl-8-(benzyloxy)-2-methyl-1-oxo-1,2,3,4-tetrahydro-pyrrolo[1,2-a]-pyrazine-7-carboxylate

Product 1

HCID 68864415HCID 68864415, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of ethyl 6-acetyl-8-(benzyloxy)-2-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]-pyrazine-7-carboxylate (0.44 g,1.2 mmol; see Example 7, Step 7), and hydrazine monohydrate (0.37 mL, 11.9 mmol) in glacial acetic acid (2 mL) was heated in a microwave oven at 180° C. for 20 minutes. The reaction mixture was concentrated under vacuum and the residue partitioned between dichloromethane and aqueous sodium bicarbonate. The organic extract was dried over MgSO4, filtered, and concentrated to provide the titled dione.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue partitioned between dichloromethane and aqueous sodium bicarbonate
  3. extractionThe organic extract
  4. dry with materialwas dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto provide the titled dione

Sources & evidence

ORD record
ord-89ce86da2c114c9fa30b88ff29a041d9
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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