Acetic Acid → HCID 66914859, compound

HRID 880447Notes

Reaction equation

HRID 880447 reaction equation
C(O)(=O)C.CN.C([O:9][C:10](=O)[CH2:11][N:12]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=[C:13]1[CH:23]=O)C.[C:26]([BH3-])#[N:27].[Na+]>O1CCCC1>[CH3:26][N:27]1[C:10](=[O:9])[CH2:11][N:12]2[CH:16]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:14]=[C:13]2[CH2:23]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6329MethylamineHCID 5003444Sodium cyanoborohydrideHCID 86654667HCID 86654667, compound

Product 1

HCID 66914859HCID 66914859, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Acetic acid was added to a solution of methylamine (0.45 mL, 5.30 mmol, 40% in water) in tetrahydrofuran (8 mL) to adjust the pH to 6. A solution of (2-formyl-4-phenyl-pyrrol-1-yl)-acetic acid ethyl ester (680 mg, 2.65 mmol) in tetrahydrofuran (4 mL) was added and the reaction mixture stirred at ambient temperature for 45 min. Sodium cyanoborohydride (0.33 g, 5.30 mmol) was added and the reaction mixture heated at 75 C for 18 h. Concentration in vacuo yielded a residue which was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford the crude product. Purification by column chromatography over silica gel (100-200 mesh) using 30% ethyl acetate in petroleum ether afforded 2-methyl-7-phenyl-1,2-dihydropyrrolo[1,2-a]pyrazin-3-one (180 mg, 30%) as a solid.

Workup

  1. temperaturethe reaction mixture heated at 75 C for 18 h
  2. concentrationConcentration in vacuo
  3. customyielded a residue which
  4. customwas partitioned between water and ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto afford the crude product
  10. customPurification by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-4400e04b92524f0d97369014d7312826
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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