Triethylamine → 3-(4-Bromophenyl)-1-(methylsulfonyl)pyrrolidine

HRID 1054606ノート

反応式

HRID 1054606 の反応式
C(N(CC)CC)C.Cl.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:20][CH2:19][NH:18][CH2:17]2)=[CH:12][CH:11]=1.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C1COCC1.O>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]2[CH2:20][CH2:19][N:18]([S:22]([CH3:21])(=[O:24])=[O:23])[CH2:17]2)=[CH:14][CH:15]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 534077083-(4-Bromophenyl)pyrrolidine hydrochloride

生成物 1

HCID 842149093-(4-Bromophenyl)-1-(methylsulfonyl)pyrrolidine収率 108.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Triethylamine (192 mg, 1.9 mmol) was added to a suspension of 3-(4-bromophenyl)pyrrolidine hydrochloride (200 mg, 0.76 mmol) in anhydrous THF (5 mL). The reaction mixture was stirred at room temperature for 5 minutes and treated with methanesulfonyl chloride (100 mg, 0.84 mmol). After the reaction mixture was stirred at room temperature for 20 hours, the mixture was diluted with water and extracted with EtOAc (2×20 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to give 3-(4-bromophenyl)-1-(methylsulfonyl)pyrrolidine (0.25 g, quantitative yield) as a solid which was used for next step directly. MS (ES+) 303.9, 305.9 (79Br M+H, 81Br M+H)+

後処理

  1. stirringAfter the reaction mixture was stirred at room temperature for 20 hours
  2. extractionextracted with EtOAc (2×20 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-7b9b9f6faf454e98898b1edb7f26ea18
出典データセット
uspto-grants-2016_07
特許番号
US09394285B2

反応ノート

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