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

HRID 895381노트

반응식

HRID 895381 반응식
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

참가 물질

8

반응물 5

HCID 13139Diethyl chlorophosphateHCID 25517Ammonium ChlorideHCID 6690391-(4-Fluorophenyl)-4-(methylsulfonyl)piperazineHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 178418339Butyllithium2회

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매4회HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-54ba7607942d48a7b0b3317f84b2e66f
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06916817B1

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