Acetic Acid → HCID 86675144, compound

HRID 1504634Notes

Reaction equation

HRID 1504634 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.C(O)(=O)C.[BH3-]C#N.[Na+]>CO.C(OCC)(=O)C>[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 acetic acid (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 ethyl acetate and washed with saturated NaHCO3 solution and brine solution. The combined ethyl acetate layer was dried over Na2SO4 and concentrated under reduced pressure to obtain a residue, which was triturated with diethyl ether/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 ethyl acetate layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto obtain a residue, which
  7. customwas triturated with diethyl ether/pentane

Sources & evidence

ORD record
ord-01bcff32d2fc46cfb8b04d2f42821c54
Source dataset
uspto-grants-2015_12
Patent number
US09215870B2

Reaction notes

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