Acetonitrile → 1-[2-(1-Benzofuran-2-yl)-2-oxoethyl]-4-[hydroxy(diphenyl)methyl]-1-azoniabicyclo[2.2.2]octane bromide

HRID 1927134ノート

反応式

HRID 1927134 の反応式
[N:1]12[CH2:8][CH2:7][C:4]([C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[OH:10])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[O:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[CH:25]=[C:24]1[C:32](=[O:35])[CH2:33][Br:34].CC#N>C(Cl)(Cl)Cl.CS(C)=O>[Br-:34].[O:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[CH:25]=[C:24]1[C:32](=[O:35])[CH2:33][N+:1]12[CH2:6][CH2:5][C:4]([C:9]([OH:10])([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)([CH2:3][CH2:2]1)[CH2:7][CH2:8]2

参加物

6

反応物 3

HCID 6342AcetonitrileHCID 27354511-(1-Benzofuran-2-Yl)-2-Bromoethan-1-OneHCID 239923851-Azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol

生成物 1

HCID 117134981-[2-(1-Benzofuran-2-yl)-2-oxoethyl]-4-[hydroxy(diphenyl)methyl]-1-azoniabicyclo[2.2.2]octane bromide収率 57.4%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 6212Chloroform溶媒

反応条件

温度
60 °C

実験手順

1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.022 g, 0.075 mmol) was diluted in CHCl3 (1.8 mL) and dispensed directly into a 1 dram vial containing 1-(1-benzofuran-2-yl)-2-bromoethanone (0.027 g, 0.112 mmol). Added CH3CN (1.2 mL), the vial was fitted with stirring bar and capped. The reaction was stirred and heated at 60° C. for 24 h and then concentrated under vacuum to give a white solid. This residue was dissolved in DMSO and purified by preparatory HPLC (without TFA) to give the title compound (0.022 g, 57.4%). LC/MS ESI RT 1.98 min, M+452

後処理

  1. customcapped
  2. stirringThe reaction was stirred
  3. concentrationconcentrated under vacuum
  4. customto give a white solid
  5. custompurified by preparatory HPLC (without TFA)

出典と根拠

ORDレコード
ord-bb087fe90b05428aa6ea2b20f8b48a4f
出典データセット
uspto-grants-2012_05
特許番号
US08183257B2

反応ノート

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