Dimethoxymethane → HCID 18977225, Verbindung

HRID 2393761Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2393761
[C:1]1([CH3:21])[C:2]([S:7]([NH:10][C:11]([CH3:20])([CH3:19])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[B].[CH3:23]OCOC>>[C:1]1([CH3:21])[C:2]([S:7]([N:10]2[C:11]([CH3:19])([CH3:20])[CH2:12][C:13]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:23]2)(=[O:8])=[O:9])=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 3

HCID 8020DimethoxymethaneHCID 5462311BoronHCID 18977226HCID 18977226, Verbindung

Produkt 1

HCID 18977225HCID 18977225, VerbindungAusbeute 99 %

Versuchsvorschrift

To a nitrogen-blanketed mixture of N-toluenesulfonyl-1,1-dimethyl-2-phenyl-ethylamine (8.30 g, 0.027 mol.) in dimethoxymethane (50 mL) was added boron trifluororo etherate (BF3 ·OEt2, 9.9 mL, 0.081 mol.). The mixture was stirred at room temperature for 12 hours while monitoring by gas chromatography. The reaction mixture was partitioned between ethyl acetate (100 mL) and water (100 mL), separated, and the organic layer is washed with saturated sodium bicarbonate (2×100 mL) and dried over sodium sulfate (Na2 SO4). The drying agent was filtered off and the filtrate was concentrated at 40°/50 torr to give 8.55 g of N-toluenesulfonyl-3,3-dimethyl-1,2,3,4-tetrahydroisoquinoline (yield=99%).

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate (100 mL) and water (100 mL)
  2. customseparated
  3. washthe organic layer is washed with saturated sodium bicarbonate (2×100 mL)
  4. dry with materialdried over sodium sulfate (Na2 SO4)
  5. filtrationThe drying agent was filtered off
  6. concentrationthe filtrate was concentrated at 40°/50 torr

Quellen und Nachweise

ORD-Eintrag
ord-aaf35b3ccf6145e7b45fec396541f801
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05808071

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