Benzene, 1-iodo-4-(trifluoromethyl)- → HCID 68731553、化合物

HRID 2382192ノート

反応式

HRID 2382192 の反応式
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[Li]CCCC.[C:17]([CH:25]1[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[OH:24][C:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1)[CH:25]1[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:36])([CH3:37])[CH3:35])=[O:32])[CH2:27][CH2:26]1

参加物

5

反応物 3

HCID 67993Benzene, 1-iodo-4-(trifluoromethyl)-HCID 10827307Tert-butyl 4-benzoylpiperidine-1-carboxylateHCID 178418339Butyllithium

生成物 1

HCID 68731553HCID 68731553、化合物収率 67.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 1-iodo-4-(trifluoromethyl)benzene (0.92 g, 3.4 mmol) in dry THF at −78° C. was added n-BuLi (3 mL, 1.6 M in hexane) dropwise and the mixture was stirred at the same temperature for 30 min. To this was added a solution of tert-butyl 4-benzoylpiperidine-1-carboxylate (1.0 g, 3.4 mmol) in minimum amount of dry THF dropwise and the resulting reaction mixture was allowed to warm up to rt over 2 h. The reaction was quenched with ammonium chloride solution, extracted with ethyl acetate, dried over anhydrous sodium sulfate and concentrated to afford tert-butyl 4-(hydroxy(phenyl)(4-(trifluoromethyl)phenyl)methyl)-piperidine-1-carboxylate (1.0 g, 66% yield) as a pale yellow solid which was used in the next step without further purification.

後処理

  1. customthe resulting reaction mixture
  2. customThe reaction was quenched with ammonium chloride solution
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-97d1c97e4a6742aabda23270c82860ad
出典データセット
uspto-grants-2012_09
特許番号
US08258306B2

反応ノート

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