Dimethyl Sulfide → Trans-2-(4-Methoxyphenyl)-3-phenyl-1-(4-methylphenylsulphonyl)aziridine

HRID 1941481

Reaktionsgleichung

Reaktionsgleichung von HRID 1941481
CSC.[CH3:4][O:5][C:6]1[CH:23]=[CH:22][C:9]([CH:10]=[N:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:8][CH:7]=1.[C:24]1([CH:30]=[N+]=[N-])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCl.C(OC)(C)(C)C.C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[CH3:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C@H:10]2[C@H:30]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:11]2[S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:22][CH:23]=1

Komponenten

7

Edukt 3

HCID 1068Dimethyl SulfideHCID 136601Benzene, (diazomethyl)-HCID 766935N-[(4-Methoxyphenyl)methylidene]-4-methylbenzene-1-sulfonamide

Produkt 1

HCID 12012745Trans-2-(4-Methoxyphenyl)-3-phenyl-1-(4-methylphenylsulphonyl)aziridineAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 21674Acetic acid, rhodium(2+) saltKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

To a stirred solution of dimethylsulphide (7 μl, 0.1 mmol), rhodium (II) acetate (2 mg, 0.005 mmol) and N-(4-methoxybenzylidene)toluene-p-sulphonamide (144 mg, 0.5 mmol) in dichloromethane (2 ml) was added phenyldiazomethane (prepared as in Example 36; 8.96 ml of a 0.067M solution in t-butylmethylether) over a period of 12 hours. Upon completion of the addition the solvent was removed in vacuo and the residue was chromatographed using silica gel eluting with 15:85 ethyl acetate:petrol to give the title compound (96 mg, 51%). δH (CDCl3) 7.62(2H), 6.75-7.45(11H,m), 4.35(1H,d,J=6 Hz), 4.18(1H,d,J=6 Hz), 3.62(3H,s), 2.35(3H,s)ppm.

Aufarbeitung

  1. customprepared as in Example 36
  2. additionUpon completion of the addition the solvent
  3. customwas removed in vacuo
  4. customthe residue was chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-fff2ba1b05d24dbb91544fb1260fe7d5
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05703246

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