Acetic Acid → HCID 69085197, compound

HRID 594388Notes

Reaction equation

HRID 594388 reaction equation
O=[C:2]([C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([O:17][CH3:18])=[CH:11][C:10]=1[O:19][CH3:20])[CH2:3][CH2:4][C:5]([O:7]C)=O.[F:21][C:22]([F:33])([F:32])[O:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][NH2:31])=[CH:26][CH:25]=1.C(O)(=O)C.[BH3-]C#N.[Na+].[OH-].[Na+]>C1COCC1.CO>[F:21][C:22]([F:32])([F:33])[O:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][N:31]2[CH:2]([C:9]3[C:14]([O:15][CH3:16])=[CH:13][C:12]([O:17][CH3:18])=[CH:11][C:10]=3[O:19][CH3:20])[CH2:3][CH2:4][C:5]2=[O:7])=[CH:26][CH:25]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 5718464-(Trifluoromethoxy)benzylamineHCID 5003444Sodium cyanoborohydrideHCID 61645017HCID 61645017, compound

Product 1

HCID 69085197HCID 69085197, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-oxo-4-(2,4,6-trimethoxyphenyl)butanoate (200 mg; 0.70 mmol; 1.0 equiv.), (4-(trifluoromethoxy)phenyl)methanamine (677 mg; 3.54 mmol; 5.0 equiv.), acetic acid (472 mg; 7.86 mmol; 11.1 equiv.), and NaBH3CN (93 mg; 1.41 mmol; 2.0 equiv.) in anh. THF (1.5 ml), and anh. MeOH (1.5 ml) was refluxed, under nitrogen, for 24 h. After cooling to rt, 15% aq. NaOH was added, and the organic solvents were removed under reduced pressure. The residue was extracted with DCM, and the mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=50/1) afforded 1-(4-(trifluoromethoxy)benzyl)-5-(2,4,6-trimethoxyphenyl)pyrrolidin-2-one as a colorless oil. LC-MS (conditions D): tR=1.08 min.; [M+H]+: 425.72 g/mol.

Workup

  1. temperaturewas refluxed, under nitrogen, for 24 h
  2. customthe organic solvents were removed under reduced pressure
  3. extractionThe residue was extracted with DCM
  4. washthe mixed organic layers were washed with brine
  5. dry with materialdried over anh. MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customPurification by FC (DCM/MeOH=50/1)

Sources & evidence

ORD record
ord-b287521dc10d41bb846f53ac738449b8
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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