Lithium diisopropylamide → 4-[2-{1-(Triphenylmethyl)-4-imidazolyl}ethenyl]-1-phenylpiperidine

HRID 443252ノート

反応式

HRID 443252 の反応式
C(OP([CH2:9][C:10]1[N:11]=[CH:12][N:13]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=1)(OCC)=O)C.[Li+].CC([N-]C(C)C)C.[CH:42]([CH:44]1[CH2:49][CH2:48][N:47]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH2:46][CH2:45]1)=O>C1COCC1>[C:28]1([C:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:13]2[CH:14]=[C:10]([CH:9]=[CH:42][CH:44]3[CH2:49][CH2:48][N:47]([C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[CH2:46][CH2:45]3)[N:11]=[CH:12]2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

参加物

5

反応物 3

HCID 2724682Lithium diisopropylamideHCID 2763175diethyl ((1-(triphenylmethyl)-1H-imidazol-4-yl)methyl)phosphonateHCID 138429921-Phenylpiperidine-4-carbaldehyde

生成物 1

HCID 702432004-[2-{1-(Triphenylmethyl)-4-imidazolyl}ethenyl]-1-phenylpiperidine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

The product from Step D is dissolved in THF and cooled to -78° C. under nitrogen. A solution of LDA in THF is added dropwise. The reaction was stirred at -78° C. for 1 h, then a solution of 4-formyl-1-phenylpiperidine from Step A is added, and the reaction warmed to room temperature overnight. The reaction is quenched with ammonium chloride solution, and extracted with ethyl acetate. The title compound is obtained after chromatography on silica gel.

後処理

  1. temperaturethe reaction warmed to room temperature overnight
  2. customThe reaction is quenched with ammonium chloride solution
  3. extractionextracted with ethyl acetate

出典と根拠

ORDレコード
ord-6927f1333699437ab602e4804ac4df68
出典データセット
uspto-grants-1999_04
特許番号
US05891889

反応ノート

読み込み中…