Potassium tert-butoxide → 5-(2-Fluoro-phenyl)-5-trifluoromethyl-[1,4]oxazepan-3-one

HRID 81599Notes

Reaction equation

HRID 81599 reaction equation
CC([O-])(C)C.[K+].Cl[CH2:8][C:9]([NH:11][C:12]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[F:26])([C:16]([F:19])([F:18])[F:17])[CH2:13][CH2:14][OH:15])=[O:10]>CC(O)(C)C.C1COCC1>[F:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:12]1([C:16]([F:19])([F:18])[F:17])[CH2:13][CH2:14][O:15][CH2:8][C:9](=[O:10])[NH:11]1

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 66666097HCID 66666097, compound

Product 1

HCID 666659335-(2-Fluoro-phenyl)-5-trifluoromethyl-[1,4]oxazepan-3-oneYield 76.1%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a refluxing solution of potassium tert-butylate (1.31 g, 11.29 mmol) in 43 ml t-BuOH was added dropwise a solution of 2-chloro-N-[1-(2-fluoro-phenyl)-3-hydroxy-1-trifluoromethyl-propyl]-acetamide (1.77 g, 5.64 mmol) in 35 ml THF over a period of 60 minutes. The reaction mixture was cooled down and quenched with 1N HCl. EtOAc was added and the organic layer was washed with brine, dried with MgSO4.H2O and evaporated. The crude product was purified on a silica gel column by eluting with hexane/EtOAc 3/1->2.5/1 to give 1.19 g of the title compound as white crystals.

Workup

  1. temperatureThe reaction mixture was cooled down
  2. customquenched with 1N HCl
  3. additionEtOAc was added
  4. washthe organic layer was washed with brine
  5. dry with materialdried with MgSO4.H2O
  6. customevaporated
  7. customThe crude product was purified on a silica gel column
  8. washby eluting with hexane/EtOAc 3/1->2.5/1

Sources & evidence

ORD record
ord-19e7f79cfc9145e98d25050565c21890
Source dataset
uspto-grants-2014_09
Patent number
US08846658B2

Reaction notes

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