Tetrahydrofuran → (S)-N-(4-(3,4-dichlorophenyl)butan-2-yl)-2-methylpropane-2-sulfinamide

HRID 1771100Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1771100
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10]/[CH:11]=[N:12]/[S@:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:14])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:19][Mg]Br.C1COCC1>C(Cl)Cl.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH:11]([NH:12][S@:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:14])[CH3:19])[CH:5]=[CH:6][C:7]=1[Cl:8]

Komponenten

6

Edukt 3

HCID 8028TetrahydrofuranHCID 89477639(NE,S)-N-[3-(3,4-dichlorophenyl)propylidene]-2-methylpropane-2-sulfinamideHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 86728181(S)-N-(4-(3,4-dichlorophenyl)butan-2-yl)-2-methylpropane-2-sulfinamideAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of Intermediate 16B (4.00 g, 13.1 mmol) in DCM (50 mL) was added slowly a solution of methylmagnesium bromide in toluene and THF (13.99 mL, 1.400 M, 19.59 mmol) and the reaction mixture was heated to reflux for 2.5 h. The reaction mixture was allowed to cool to rt and, diluted with DCM, washed with saturated NH4Cl, and the organic portion dried over MgSO4, filtered and concentrated. The residue was purified by ISCO chromatography (EtOAc/Hexanes 0-50% over 30 min, column 330 g, flow rate 100 mL/min) to give Intermediate 16C (2.80 g, 8.69 mmol, 67.0% yield) as a white solid. HPLC/MS (Method D) RT=1.12 min, [M+1]+ 322.1; Chiral HPLC (Method L) RT=4.55 min, PA=100%.

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 2.5 h
  3. washwashed with saturated NH4Cl
  4. dry with materialthe organic portion dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by ISCO chromatography (EtOAc/Hexanes 0-50% over 30 min, column 330 g, flow rate 100 mL/min)

Quellen und Nachweise

ORD-Eintrag
ord-9820edc57d744352bf96f2a271ba9c8b
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249096B2

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