p-Bromobenzenesulfonyl chloride → 4-Bromo-N-(6,6-dimethylbicyclo[3.1.1]heptan-2-yl)benzene sulfonamide

HRID 2046059

Reaktionsgleichung

Reaktionsgleichung von HRID 2046059
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][C:13]1([CH3:22])[C@H:18]2[CH2:19][C@@H:14]1[CH2:15][CH2:16][C@H:17]2CN.CC[N:25](CC)CC>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:25][CH:17]2[CH2:16][CH2:15][CH:14]3[CH2:19][CH:18]2[C:13]3([CH3:22])[CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 11194443Myrtanylamine, cis-(-)-

Produkt 1

HCID 666149414-Bromo-N-(6,6-dimethylbicyclo[3.1.1]heptan-2-yl)benzene sulfonamideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 4-bromo-benzenesulphonyl chloride (0.6 g, 2.34 mmol) in anhydrous CH2Cl2 (5 ml) and Et3N (0.65 ml, excess) at 0° C. was added (−) cis-myrtanylamine (0.36 g, 2.34 mmol) and the stirring was continued overnight at room temperature. The reaction mixture was diluted with CH2Cl2 (15 ml) and washed with H2O (2×100 ml). The organic layer was separated and dried over MgSO4 and the solvent was distilled to afford the title compound (0.87 g, 100%), as pale paste, which was solidified on standing. 1H-NMR (CDCl3) 7.70 (d, 2H, J=6.78 Hz); 6.64 (d, 2H, J=6.90 Hz); 2.91 (t, 2H, J=7.59 Hz); 2.32-2.29 (m, 1H); 2.11-2.06 (m, 1H); 1.91-1.81 (m, 6H); 1.39-1.31 (m, 1H); 1.11 (s, 3H); 0.86 (s, 3H).

Aufarbeitung

  1. washwashed with H2O (2×100 ml)
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. distillationthe solvent was distilled

Quellen und Nachweise

ORD-Eintrag
ord-f662ad1cec05482eb23e8437292f6113
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592399B2

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