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

HRID 338263Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 338263
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

Komponenten

6

Edukt 3

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

Produkt 1

HCID 842149093-(4-Bromophenyl)-1-(methylsulfonyl)pyrrolidineAusbeute 108,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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)+

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-316407eb581a4b65a5117f156cf0cb44
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889730B2

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