Ammonium formate → HCID 66584850, compound

HRID 589884Notes

Reaction equation

HRID 589884 reaction equation
Cl[C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][C:5]2=[C:4]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:3]=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=1.C([O-])=O.[NH4+]>CO.[Pd]>[F:29][C:25]1[CH:24]=[C:23]([C:3]2[C:4]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:5]3[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])[CH2:8][CH2:7][N:6]3[CH:2]=2)[CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 66585014HCID 66585014, compound

Product 1

HCID 66584850HCID 66584850, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 6.00 g (14.2 mmol) of 2-tert-butyl 8-ethyl 6-chloro-7-(3-fluorophenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxylate, 13.4 g (212 mmol) of ammonium formate (CAS 540-69-2) and 0.6 g of 10% palladium-on-charcoal containing 50% water in 50 ml of methanol is stirred at reflux for 45 minutes. After cooling, the mixture is filtered through a Büchner funnel and the filtrate is concentrated under reduced pressure. The residue is taken up in ethyl acetate, the solution is washed with aqueous 2N sodium hydroxide solution and then dried over sodium sulfate, and the solvent is evaporated off under reduced pressure, to give 5.5 g of 2-tert-butyl 8-ethyl 7-(3-fluorophenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxylate in the form of a yellow oil.

Workup

  1. temperatureat reflux for 45 minutes
  2. temperatureAfter cooling
  3. filtrationthe mixture is filtered through a Büchner funnel
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. washthe solution is washed with aqueous 2N sodium hydroxide solution
  6. dry with materialdried over sodium sulfate
  7. customthe solvent is evaporated off under reduced pressure

Sources & evidence

ORD record
ord-d1628503dfdd48c2b06f49110d2287f3
Source dataset
uspto-grants-2016_01
Patent number
US09233965B2

Reaction notes

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