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Sodium Iodide → (S)-3-(4-nitrobenzoyloxy)-1-[3-(4-methoxyphenyl)propyl]pyrrolidine

HRID 1859455
ノート
印刷プレビュー

反応式

HRID 1859455 の反応式
S(O[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)(=O)(=O)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].[N+:25]([C:28]1[CH:41]=[CH:40][C:31]([C:32]([O:34][C@H:35]2[CH2:39][CH2:38][NH:37][CH2:36]2)=[O:33])=[CH:30][CH:29]=1)([O-:27])=[O:26]>C(#N)C>[N+:25]([C:28]1[CH:41]=[CH:40][C:31]([C:32]([O:34][C@H:35]2[CH2:39][CH2:38][N:37]([CH2:6][CH2:7][CH2:8][C:9]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=3)[CH2:36]2)=[O:33])=[CH:30][CH:29]=1)([O-:27])=[O:26]
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 116659383-(4-Methoxyphenyl)propyl methanesulfonateHCID 12148704(S)-3-(4-nitrobenzoyloxy)pyrrolidine

生成物 1

HCID 69900894(S)-3-(4-nitrobenzoyloxy)-1-[3-(4-methoxyphenyl)propyl]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

3-(4-Methoxyphenyl)propyl mesylate (732 mg, 3.00 mmol), sodium carbonate (320 mg, 3.00 mmol) and sodium iodide (30 mg, 0.20 mmol) were added to a solution of (S)-3-(4-nitrobenzoyloxy)pyrrolidine (472 mg, 2.00 mmol) in acetonitrile (25 ml), and they were heated under reflux at 90° C. for 6 hours. 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-[3-(4-methoxyphenyl)propyl]pyrrolidine in the form of a light yellow oil (507 mg, 66%).

後処理

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

出典と根拠

ORDレコード
ord-cffe82c9197f4fa5a798ec2e6086049d
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

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