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

HRID 242036ノート

反応式

HRID 242036 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7799b6616b79475f8cbd3c32f0a4d92b
出典データセット
uspto-grants-2014_02
特許番号
US08653102B2

反応ノート

読み込み中…