Phenacyl bromide → 3-((Bis(3-fluorophenyl)methoxy)carbonyl)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide

HRID 1910499

반응식

HRID 1910499 반응식
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([C:9]([O:11][CH:12]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)=[O:10])[CH2:2]2.[Br:27][CH2:28][C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:30]>C(#N)C>[Br-:27].[F:26][C:22]1[CH:21]=[C:20]([CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)[O:11][C:9]([CH:3]2[CH:4]3[CH2:5][CH2:6][N+:1]([CH2:28][C:29](=[O:30])[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)([CH2:8][CH2:7]3)[CH2:2]2)=[O:10])[CH:25]=[CH:24][CH:23]=1

참가 물질

4

반응물 2

HCID 6259Phenacyl bromideHCID 70925896Bis(3-fluorophenyl)methyl quinuclidine-3-carboxylate

생성물 1

HCID 866729363-((Bis(3-fluorophenyl)methoxy)carbonyl)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide수율 73.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Bis(3-fluorophenyl)methyl quinuclidine-3-carboxylate (95 mg, 0.27 mmol, prepared as in example 4) and 2-bromo-1-phenylethanone (58.2 mg, 0.29 mmol) were dissolved in acetonitrile (5 ml) and stirred at room temperature overnight. The solvent was evaporated, and the resulting residue was purified by flash chromatography (DCM/MeOH=95/5 to 9/1) to obtain 3-((bis(3-fluorophenyl)methoxy)carbonyl)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (110 mg, racemic mixture).

후처리

  1. customThe solvent was evaporated
  2. customthe resulting residue was purified by flash chromatography (DCM/MeOH=95/5 to 9/1)

출처 및 근거

ORD 기록
ord-56119211b8554d588e5c2f8510d25183
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604015B2

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