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

HRID 2196317Notes

Reaction equation

HRID 2196317 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-4742c8c8633c48319eab873e00e6f038
Source dataset
uspto-grants-2012_12
Patent number
US08338413B1

Reaction notes

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