7-Azabicyclo[4.1.0]heptane, 7-[(4-methylphenyl)sulfonyl]- → 4-Methyl-N-(trans-2-methyl-cyclohexyl)-benzenesulfonamide

HRID 1750228

Reaktionsgleichung

Reaktionsgleichung von HRID 1750228
[C:1]1([CH3:17])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH:16]3[CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15]3)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:18][Li]>C1COCC1.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.[Cu]>[CH3:17][C:1]1[CH:2]=[CH:3][C:4]([S:7]([NH:10][C@@H:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]2[CH3:18])(=[O:8])=[O:9])=[CH:5][CH:6]=1

Komponenten

5

Edukt 2

HCID 118318857-Azabicyclo[4.1.0]heptane, 7-[(4-methylphenyl)sulfonyl]-HCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 155078474-Methyl-N-(trans-2-methyl-cyclohexyl)-benzenesulfonamideAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5363992Copper, bis(2,4-pentanedionato-O,O')-, (SP-4-1)-KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To the solution of 180 g of) 7-(Toluene-4-sulfonyl)-7-aza-bicyclo[4.1.0]heptane and 18 g of Copper(II)acetyl acetonate in 1500 ml of dry THF was added 86 ml of a 10 M solution of methyllithium dropwise over 30 min. The mixture was stirred under nitrogen atmosphere for 8 h. It was then washed with water and extracted with ethyl acetate twice. The combined organic layers were concentrated. The resulting residue was purified by chromatography (silica, hexan/ethyl acetate) to afford 120 g (62%) of 4-Methyl-N-(trans-2-methyl-cyclohexyl)-benzenesulfonamide

Aufarbeitung

  1. washIt was then washed with water
  2. extractionextracted with ethyl acetate twice
  3. concentrationThe combined organic layers were concentrated
  4. customThe resulting residue was purified by chromatography (silica, hexan/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-7bc686e44169495298bb440529623f9f
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156796B2

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