Diethyl chlorophosphate → 4-(4-Fluorophenyl)-1-[2-(1-t-butoxycarbonylpiperidin-4-yl)-ethenylsulphonyl]-piperazine

HRID 895381ノート

反応式

HRID 895381 の反応式
C([Li])CCC.[F:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][N:16]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1.C(OP(Cl)(OCC)=O)C.[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][CH:42]([CH:45]=O)[CH2:41][CH2:40]1)=[O:38])([CH3:35])([CH3:34])[CH3:33].[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[F:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[CH2:18][CH2:17][N:16]([S:19]([CH:22]=[CH:45][CH:42]3[CH2:43][CH2:44][N:39]([C:37]([O:36][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:38])[CH2:40][CH2:41]3)(=[O:20])=[O:21])[CH2:15][CH2:14]2)=[CH:11][CH:12]=1

参加物

8

反応物 5

HCID 13139Diethyl chlorophosphateHCID 25517Ammonium ChlorideHCID 6690391-(4-Fluorophenyl)-4-(methylsulfonyl)piperazineHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 178418339Butyllithium2 回

生成物 1

HCID 541807894-(4-Fluorophenyl)-1-[2-(1-t-butoxycarbonylpiperidin-4-yl)-ethenylsulphonyl]-piperazine

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒4 回HCID 8857Ethyl Acetate溶媒

実験手順

n-Butyl lithium (8.6 ml of a 1.6 M solution in THF) was added dropwise to a suspension of 4-(4-fluorophenyl)-1-methanesulphonylpiperazine (3.52 g) in THF (40 ml) at −78° C. and the mixture was stirred for 30 minutes. Diethylchlorophosphate (1.97 ml) was added dropwise and the mixture was stirred at −78° C. for a further 30 minutes. n-Butyl lithium (8.6 ml of a 1.6 M solution in THF) was added dropwise and stirred for 30 minutes. A solution of 1-(t-butoxycarbonyl)-piperidine-4-aldehyde (2.91 g) in THF (5 ml) was added dropwise and the mixture was allowed to warm to ambient temperature and was stired for 10 hours. Saturated aqueous ammonium chloride solution (5 ml) was added, the reaction mixture was diluted with ethyl acetate (25 ml) and washed with water. Removal of the solvent gave 4-(4-fluorophenyl)-1-[2-(1-t-butoxycarbonylpiperidin-4-yl)-ethenylsulphonyl]-piperazine as a gum which solidified on standing, M+H=455 (454).

後処理

  1. stirringthe mixture was stirred at −78° C. for a further 30 minutes
  2. stirringstirred for 30 minutes
  3. waitwas stired for 10 hours
  4. washwashed with water
  5. customRemoval of the solvent

出典と根拠

ORDレコード
ord-54ba7607942d48a7b0b3317f84b2e66f
出典データセット
uspto-grants-2005_07
特許番号
US06916817B1

反応ノート

読み込み中…