Hydrochloric Acid → HCID 131730283, compound

HRID 874915Notes

Reaction equation

HRID 874915 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH:6]1[N:11]2[CH:12]=[C:13]([N+:15]([O-])=O)[CH:14]=[C:10]2[C:9](=[O:18])[NH:8][CH2:7]1)[CH3:2].[ClH:20]>C(O)C.[Pd]>[ClH:20].[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH:6]1[N:11]2[CH:12]=[C:13]([NH2:15])[CH:14]=[C:10]2[C:9](=[O:18])[NH:8][CH2:7]1)[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131730285HCID 131730285, compound

Product 1

HCID 131730283HCID 131730283, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl(7-nitro-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl)acetate (V, where R1=OCH2CH3) (0.55 g, 2.1 mmol) in ethanol 100% (20 mL) was added hydrochloric acid (4 M solution in 1,4-dioxane, 0.52 mL, 2.1 mmol). The reaction mixture was stirred at room temperature in the presence of Pd—C (10%) (0.11 g), under hydrogen atmosphere (50 psi). After 7 h the solid was filtered through celite (washed with ethanol) and the solvent evaporated under vacuum, to obtain compound ethyl(7-amino-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl)acetate hydrochloride (I) as a light-brown solid (0.56 g, 98% yield), used without further purification in the next steps. Very hygroscopic product. To be stored for a short time and under inert gas atmosphere.

Workup

  1. filtrationAfter 7 h the solid was filtered through celite (washed with ethanol)
  2. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-a8ac63a1382e4a5e827e76c733a2ca3c
Source dataset
uspto-grants-2015_03
Patent number
US08981092B2

Reaction notes

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