Acetic Anhydride → HCID 59373920, compound

HRID 473727Notes

Reaction equation

HRID 473727 reaction equation
[F:1][C:2]1[C:7]([CH:8]2[CH2:12][CH2:11][NH:10][CH2:9]2)=[N:6][CH:5]=[CH:4][N:3]=1.[C:13](OC(=O)C)(=[O:15])[CH3:14].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:1][C:2]1[C:7]([CH:8]2[CH2:12][CH2:11][N:10]([C:13](=[O:15])[CH3:14])[CH2:9]2)=[N:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 67425692HCID 67425692, compound

Product 1

HCID 59373920HCID 59373920, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-fluoro-3-(pyrrolidin-3-yl)pyrazine (0.2 g, 1.2 mmol) dissolved in DCM (2.4 mL) was added acetic anhydride (0.56 mL, 6.0 mmol) and sodium bicarbonate (0.502 g, 5.98 mmol). The reaction mixture was stirred at RT under N2 for 3 h. The reaction mixture was partitioned between 1N NaOH and DCM. The aqueous layer was back extracted with DCM (3×) and the combined DCM layer was washed with brine, dried (Na2SO4) and concentrated to provide 1-(3-(3-fluoropyrazin-2-yl)pyrrolidin-1-yl)ethanone as a yellow oil. MS (ESI, pos. ion) m/z: 210.0 (M+1).

Workup

  1. customThe reaction mixture was partitioned between 1N NaOH and DCM
  2. extractionThe aqueous layer was back extracted with DCM (3×)
  3. washthe combined DCM layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9a10cc71c29546d8b3729bbb94b7984d
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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