Ammonium Chloride → HCID 68495138, compound

HRID 1173460Notes

Reaction equation

HRID 1173460 reaction equation
[CH3:1][C:2]([CH3:21])([CH3:20])[CH2:3][N:4]([CH2:17][CH:18]=[O:19])[C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([C:13]([F:16])([F:15])[F:14])[CH:6]=1.[BH4-].[Na+].[NH4+].[Cl-]>CO>[CH3:1][C:2]([CH3:21])([CH3:20])[CH2:3][N:4]([CH2:17][CH2:18][OH:19])[C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([C:13]([F:14])([F:15])[F:16])[CH:6]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 11289510HCID 11289510, compound

Product 1

HCID 68495138HCID 68495138, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[(2,2-dimethylpropyl)(2-oxoethyl)amino]-2-(trifluoromethyl)benzonitrile (0.882 g, 2.96 mmol) in MeOH (10 mL) at 0° C. was added NaBH4 (0.112 g, 2.96 mmol) in one portion and the mixture was stirred overnight, slowly warming to rt. The mixture was cooled to 0° C., sat'd NH4Cl (1 mL) was added and the mixture was concentrated in vacuo. The residue was partitioned between EtOAc/water and the layers were separated. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording 0.829 g of the title compound as a colorless syrup which solidified on standing: MS (ESI) m/z 301 (M+1).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe residue was partitioned between EtOAc/water
  4. customthe layers were separated
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-1f11d0d3edd148cf8f97c2f27e396e6d
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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