Ammonium Chloride → Ethyl 1-benzyl-5,5-difluoro-4-oxopiperidine-3-carboxylate

HRID 451557ノート

反応式

HRID 451557 の反応式
[CH2:1]([N:8]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:9][C:10]([F:17])([F:16])[C:11]([O:13]CC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[NH4+].[Cl-]>CN1C(=O)CCC1>[CH2:1]([N:8]1[CH2:9][C:10]([F:16])([F:17])[C:11](=[O:13])[CH:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:18]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 59442745Ethyl 3-(benzyl(3-ethoxy-3-oxopropyl)amino)-2,2-difluoropropanoate

生成物 1

HCID 49761228Ethyl 1-benzyl-5,5-difluoro-4-oxopiperidine-3-carboxylate収率 60%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

To a solution of ethyl 3-(benzyl(3-ethoxy-3-oxopropyl)amino)-2,2-difluoropropanoate (10.78 g, 31.4 mmol) in NMP (100 mL) at 0° C. was added potassium tert-butoxide (5.64 g, 50.2 mmol) and the reaction mixture stirred at room temperature for 2 days. The reaction mixture was cooled to 0° C. and aqueous NH4Cl solution was added. The aqueous phase was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and the solvent was evaporated. The residue was purified by flash chromatography using a gradient EtOAc/Heptane 0-70% over 40 minutes to give the title compound as white solid (5.56 g, 60%).

後処理

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. extractionThe aqueous phase was extracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customthe solvent was evaporated
  5. customThe residue was purified by flash chromatography
  6. customover 40 minutes

出典と根拠

ORDレコード
ord-dcf895ba3783482e8284fa963b906185
出典データセット
uspto-grants-2013_07
特許番号
US08486967B2

反応ノート

読み込み中…