Tetrahydro-4H-pyran-4-one → 1-(2-(tetrahydro-2H-pyran-4-ylamino)-4-(trifluoromethyl)phenyl)ethanone

HRID 242036Notes

Reaction equation

HRID 242036 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].[O:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1.[B][B][B][B][B][B][B][B][B][B].CCOC(C)=O.CCCCCC>CO>[O:15]1[CH2:20][CH2:19][CH:18]([NH:1][C:2]2[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[CH:4][C:3]=2[C:12](=[O:14])[CH3:13])[CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 21226206Ethyl acetate hexaneHCID 468355001-(2-Amino-4-(trifluoromethyl)phenyl)ethan-1-oneHCID 178419135HCID 178419135, compound

Product 1

HCID 665846701-(2-(tetrahydro-2H-pyran-4-ylamino)-4-(trifluoromethyl)phenyl)ethanoneYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 500 mg (2.46 mmol) 1-(2-amino-4-(trifluoromethyl)phenyl)ethanone in methanol (18 ml) was added 250 μl (2.70 mmol) dihydro-2H-pyran-4(3H)-one at RT followed by the addition of 90 mg (0.73 mmol) decaborane. The reaction mixture was stirred at RT for 16 h. The mixture was evaporated under vacuum and residue diluted with ethyl acetate (20 ml). The organic layer was washed with water (20 ml), brine (20 ml), dried over anhydrous Na2SO4 and concentrated in vacuum. After CC (EtOAc/hexane 1:24) of the residue, 240 mg (0.83 mmol, 34%) 1-(2-(tetrahydro-2H-pyran-4-ylamino)-4-(trifluoromethyl)phenyl)ethanone were obtained.

Workup

  1. customThe mixture was evaporated under vacuum and residue
  2. additiondiluted with ethyl acetate (20 ml)
  3. washThe organic layer was washed with water (20 ml), brine (20 ml)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-7799b6616b79475f8cbd3c32f0a4d92b
Source dataset
uspto-grants-2014_02
Patent number
US08653102B2

Reaction notes

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