N-(6,6-dimethyl bicyclo[3.1.1]heptan-2-yl)-4-(4-hydroxybut-1-ynyl)benzenesulphonamide → N-(6,6-Dimethylbicyclo[3.1.1]heptan-2-yl)-4-(4-hydroxybutyl)benzene sulfonamide

HRID 717644

Reaktionsgleichung

Reaktionsgleichung von HRID 717644
[CH3:1][C:2]1([CH3:24])[CH:7]2[CH2:8][CH:3]1[CH2:4][CH2:5][CH:6]2[NH:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([C:19]#[C:20][CH2:21][CH2:22][OH:23])=[CH:15][CH:14]=1)(=[O:12])=[O:11]>CCO.[Pd]>[CH3:1][C:2]1([CH3:24])[CH:7]2[CH2:8][CH:3]1[CH2:4][CH2:5][CH:6]2[NH:9][S:10]([C:13]1[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][CH2:21][CH2:22][OH:23])=[CH:17][CH:18]=1)(=[O:12])=[O:11]

Komponenten

4

Edukt 1

HCID 66614933N-(6,6-dimethyl bicyclo[3.1.1]heptan-2-yl)-4-(4-hydroxybut-1-ynyl)benzenesulphonamide

Produkt 1

HCID 66614961N-(6,6-Dimethylbicyclo[3.1.1]heptan-2-yl)-4-(4-hydroxybutyl)benzene sulfonamideAusbeute 104,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of the product of Step B (0.11 g, 0.3 mmol) and 10% Pd/C (0.06 g) in EtOH (10 ml) was stirred for 16 h under H2. The catalyst was filtered through Celite pad and the filtrate evaporated to dryness to give the title compound (0.11 g, 100%,) as creamy gum. 1H-NMR (CDCl3) 7.74 (d, 2H, J=7.89 Hz); 7.29 (d, 2H, J=8.01 Hz); 4.9 (bs, 1H, NH); 3.71-3.65 (m, 2H); 2.92-2.87 (m, 2H); 2.70 (t, 2H, J=7.74 Hz); 2.45-2.30 (m, 1H); 2.25-2.10 (m, 1H); 1.86-1.58 (m, 9H); 1.3-1.1 (m, 2H); 1.08 (s, 3H); 0.83 (s, 3H).

Aufarbeitung

  1. filtrationThe catalyst was filtered through Celite pad
  2. customthe filtrate evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-e164d3571644497b86658e4313f6b086
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193716B2

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