4-Cyclopropylaniline → 2,5-Bis(4-bromophenyl)-1-(4-cyclopropylphenyl)pyrrolidine

HRID 1470964ノート

反応式

HRID 1470964 の反応式
CS(O[CH:6]([C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=1)[CH2:7][CH2:8][CH:9](OS(C)(=O)=O)[C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=1)(=O)=O.[CH:29]1([C:32]2[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=2)[CH2:31][CH2:30]1>CN(C=O)C>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([CH:9]2[CH2:8][CH2:7][CH:6]([C:22]3[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=3)[N:36]2[C:35]2[CH:37]=[CH:38][C:32]([CH:29]3[CH2:31][CH2:30]3)=[CH:33][CH:34]=2)=[CH:11][CH:12]=1

参加物

4

反応物 2

HCID 122539274-CyclopropylanilineHCID 582265311,4-Bis(4-bromophenyl)butane-1,4-diyl dimethanesulfonate

生成物 1

HCID 672363922,5-Bis(4-bromophenyl)-1-(4-cyclopropylphenyl)pyrrolidine収率 76%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

The product from Example 42B (3.14 g, 5.64 mmol) and 4-cyclopropylaniline (6.01 g, 45.2 mmol) were combined in DMF (20 mL). The mixture was stirred at 50° C. under nitrogen for 3 hours. The reaction mixture was partitioned between 1M HCl and ethyl acetate. The organic layer was washed with brine three times, dried with sodium sulfate, filtered and evaporated. The residue was purified by chromatography on silica gel eluting with ethyl acetate/hexane (0.5% to 1%) to give the title compound (2.12 g, 76%) as a mixture of stereoisomers as a sticky solid.

後処理

  1. customThe reaction mixture was partitioned between 1M HCl and ethyl acetate
  2. washThe organic layer was washed with brine three times
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel eluting with ethyl acetate/hexane (0.5% to 1%)

出典と根拠

ORDレコード
ord-17d648c98f47420a9db69c33ebb5a368
出典データセット
uspto-grants-2015_04
特許番号
US09006387B2

反応ノート

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