4-Bromobenzoic acid → N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-4-bromobenzamide

HRID 891434ノート

反応式

HRID 891434 の反応式
Cl.Cl.[N:3]12[CH2:10][CH2:9][CH:6]([CH2:7][CH2:8]1)[C@@H:5]([NH2:11])[CH2:4]2.[Br:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=1>>[N:3]12[CH2:10][CH2:9][CH:6]([CH2:7][CH2:8]1)[C@@H:5]([NH:11][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][C:13]([Br:12])=[CH:14][CH:15]=1)[CH2:4]2

参加物

3

反応物 2

HCID 114644-Bromobenzoic acidHCID 12494972(R)-(+)-3-Aminoquinuclidine Dihydrochloride

生成物 1

HCID 11461014N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-4-bromobenzamide

実験手順

Prepared by a method analogous to that described for the preparation of Intermediate 1 from (R)-1-azabicyclo[2.2.2]oct-3-ylamine dihydrochloride and 4-bromobenzoic acid; the compound was purified by chromatography on silica gel using ammoniated methanol/chloroform mixtures as the eluent. The compound was then dissolved in tetrahydrofuran, excess hydrogen chloride (1M solution in diethyl ether) was added, and the solution was evaporated and then recrystallised from methanol/t-butyl methyl ether to give the hydrochloride salt of the title compound as a colourless solid; MS (ES+) 309, 311 (MH+).

後処理

  1. customPrepared by a method analogous to
  2. customthe compound was purified by chromatography on silica gel using ammoniated methanol/chloroform mixtures as the eluent
  3. dissolutionThe compound was then dissolved in tetrahydrofuran
  4. additionexcess hydrogen chloride (1M solution in diethyl ether) was added
  5. customthe solution was evaporated
  6. customrecrystallised from methanol/t-butyl methyl ether

出典と根拠

ORDレコード
ord-c1c67c44cd424befa4fabc251d69e9fb
出典データセット
uspto-grants-2006_02
特許番号
US07001914B2

反応ノート

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