2-Chloroacetophenone → (3R)-1-(2-oxo-2-phenylethyl)-3-(2-(2-oxopyrrolidin-1-yl)-2-phenylacetoxy)-1-azoniabicyclo[2.2.2]octane chloride

HRID 404667노트

반응식

HRID 404667 반응식
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[O:11]=[C:12]1[CH2:16][CH2:15][CH2:14][N:13]1[CH:17]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:18]([O:20][C@@H:21]1[CH:26]2[CH2:27][CH2:28][N:23]([CH2:24][CH2:25]2)[CH2:22]1)=[O:19]>CCOC(C)=O.C(#N)C>[Cl-:1].[O:4]=[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:2][N+:23]12[CH2:24][CH2:25][CH:26]([CH2:27][CH2:28]1)[C@@H:21]([O:20][C:18](=[O:19])[CH:17]([N:13]1[CH2:14][CH2:15][CH2:16][C:12]1=[O:11])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:22]2

참가 물질

5

반응물 2

HCID 107572-ChloroacetophenoneHCID 86688927(R)-quinuclidin-3-yl 2-(2-oxopyrrolidin-1-yl)-2-phenylacetate

생성물 1

HCID 86688928(3R)-1-(2-oxo-2-phenylethyl)-3-(2-(2-oxopyrrolidin-1-yl)-2-phenylacetoxy)-1-azoniabicyclo[2.2.2]octane chloride수율 67.9%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

2-Chloro-1-phenylethanone (62.1 mg, 0.40 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-(2-oxopyrrolidin-1-yl)-2-phenylacetate (120 mg, 0.36 mmol) in EtOAc (2.4 ml) and acetonitrile (1.2 ml). The pale yellow solution was stirred at room temperature for three days. The solvent was evaporated and the crude was purified by flash chromatography (DCM/MeOH=9/1) to collect the title compound (118 mg, 66.9% yield) as an off-white spongy solid.

후처리

  1. customThe solvent was evaporated
  2. customthe crude was purified by flash chromatography (DCM/MeOH=9/1)

출처 및 근거

ORD 기록
ord-6a8866aedb5848b7be26458da4bbc8f4
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748613B2

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