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

HRID 1054606노트

반응식

HRID 1054606 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 842149093-(4-Bromophenyl)-1-(methylsulfonyl)pyrrolidine수율 108.1%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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)+

후처리

  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

출처 및 근거

ORD 기록
ord-7b9b9f6faf454e98898b1edb7f26ea18
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394285B2

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