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Sodium Iodide → (S)-3-(4-Nitrobenzoyloxy)-1-(4-methoxyphenethyl)pyrrolidine

HRID 1859444
ノート
印刷プレビュー

反応式

HRID 1859444 の反応式
S(C1C=CC(C)=CC=1)(O[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].[N+:30]([C:33]1[CH:46]=[CH:45][C:36]([C:37]([O:39][C@H:40]2[CH2:44][CH2:43][NH:42][CH2:41]2)=[O:38])=[CH:35][CH:34]=1)([O-:32])=[O:31]>C(#N)C>[N+:30]([C:33]1[CH:46]=[CH:45][C:36]([C:37]([O:39][C@H:40]2[CH2:44][CH2:43][N:42]([CH2:5][CH2:6][C:7]3[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=3)[CH2:41]2)=[O:38])=[CH:35][CH:34]=1)([O-:32])=[O:31]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 2853842-(4-Methoxyphenyl)ethyl 4-methylbenzenesulfonateHCID 12148704(S)-3-(4-nitrobenzoyloxy)pyrrolidine

生成物 1

HCID 69901303(S)-3-(4-Nitrobenzoyloxy)-1-(4-methoxyphenethyl)pyrrolidine

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒

反応条件

温度
90 °C

実験手順

4-Methoxyphenethyl tosylate (1.24 g, 4.05 mmol), sodium carbonate (430 mg, 4.06 mmol) and sodium iodide (40 mg, 0.26 mmol) were added to a solution of (S)-3-(4-nitrobenzoyloxy)pyrrolidine (799 mg, 3.38 mmol) in acetonitrile (40 ml), and they were heated under reflux at 90° C. for 3 hours. The insoluble material was removed by the filtration. The insoluble material was washed with ethyl acetate, and the wash solution was combined with the filtrate. The solvent was evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography. The product was eluted with hexane and ethyl acetate (10:1) and then with a mixture of the same solvents (1:1). The appropriate fractions were combined, and the solvent was evaporated under reduced pressure to obtain (S)-3-(4-nitrobenzoyloxy)-1-(4-methoxy-phenethyl)pyrrolidine in the form of a light yellow oil (1.00 g, 80%).

後処理

  1. temperaturewere heated
  2. customThe insoluble material was removed by the filtration
  3. washThe insoluble material was washed with ethyl acetate
  4. customThe solvent was evaporated under reduced pressure
  5. washThe product was eluted with hexane and ethyl acetate (10:1)
  6. additionwith a mixture of the same solvents (1:1)
  7. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-aaf43faa9e074a3eba372d6a44c7e83b
出典データセット
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06528504B2

反応ノート

読み込み中…

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