Acetic Acid → HCID 86675144, compound

HRID 587683Notes

Reaction equation

HRID 587683 reaction equation
[Br:1][C:2]1[CH:16]=[C:15](/[CH:17]=[CH:18]/[CH:19]([C:24]2[CH:29]=[C:28]([Cl:30])[C:27]([Cl:31])=[C:26]([Cl:32])[CH:25]=2)[C:20]([F:23])([F:22])[F:21])[CH:14]=[CH:13][C:3]=1[C:4]([NH:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)=[O:5].[O:33]1[CH2:36][C:35](=O)[CH2:34]1.CC(O)=O.[BH3-]C#N.[Na+]>CO.CCOC(C)=O>[Br:1][C:2]1[CH:16]=[C:15](/[CH:17]=[CH:18]/[CH:19]([C:24]2[CH:25]=[C:26]([Cl:32])[C:27]([Cl:31])=[C:28]([Cl:30])[CH:29]=2)[C:20]([F:23])([F:21])[F:22])[CH:14]=[CH:13][C:3]=1[C:4]([NH:6][CH:7]1[CH2:12][CH2:11][N:10]([CH:35]2[CH2:36][O:33][CH2:34]2)[CH2:9][CH2:8]1)=[O:5]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 150242543-OxetanoneHCID 86675137HCID 86675137, compound

Product 1

HCID 86675144HCID 86675144, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (E)-2-bromo-N-(piperidin-4-yl)-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)benzamide (0.2 g, 0.35 mmol), oxetan-3-one (0.027 g, 0.38 mmol) and AcOH (0.01 mL) in MeOH (5.0 mL) was stirred at ambient temperature for 30 min. After that NaBH3CN (0.022 g, 0.35 mmol) was added at 0° C. slowly lot wise over the period of 10 min and the reaction was stirred for 8 h at ambient temperature. The solvent was removed under reduced pressure to obtain a residue which was diluted with EtOAc and washed with saturated NaHCO3 solution and brine solution. The combined EtOAc layer was dried over Na2SO4 and concentrated under reduced pressure to obtain a residue, which was triturated with Et2O/pentane to afford the title compound as an off-white solid (0.05 g, 23%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto obtain a residue which
  3. washwashed with saturated NaHCO3 solution and brine solution
  4. dry with materialThe combined EtOAc layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto obtain a residue, which
  7. customwas triturated with Et2O/pentane

Sources & evidence

ORD record
ord-d262d455350442a6ab66227c3bb7af44
Source dataset
uspto-grants-2016_01
Patent number
US09226501B2

Reaction notes

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