3-Butyn-1-OL → N-(6,6-dimethyl bicyclo[3.1.1]heptan-2-yl)-4-(4-hydroxybut-1-ynyl)benzenesulphonamide

HRID 2046060

Reaktionsgleichung

Reaktionsgleichung von HRID 2046060
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]2[CH2:17][CH2:16][CH:15]3[CH2:18][CH:13]2[C:14]3([CH3:20])[CH3:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:21]([OH:25])[CH2:22][C:23]#[CH:24]>CN(C=O)C.CCN(C(C)C)C(C)C>[CH3:19][C:14]1([CH3:20])[CH:13]2[CH2:18][CH:15]1[CH2:16][CH2:17][CH:12]2[NH:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([C:24]#[C:23][CH2:22][CH2:21][OH:25])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Komponenten

5

Edukt 2

HCID 135663-Butyn-1-OLHCID 666149414-Bromo-N-(6,6-dimethylbicyclo[3.1.1]heptan-2-yl)benzene sulfonamide

Produkt 1

HCID 66614933N-(6,6-dimethyl bicyclo[3.1.1]heptan-2-yl)-4-(4-hydroxybut-1-ynyl)benzenesulphonamideAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 81531DiisopropylethylamineLösungsmittel

Versuchsvorschrift

A solution of the product of Step A (0.37 g, 0.5 mmol) and but-3-yn-1-ol (0.12 ml, excess) in a mixture of DMF (5 ml) and DIPEA (0.5 ml) was degassed with N2 and Cl2Pd(PPh3)2 (0.07 g) was added, followed by catalytic amount of CuI and the mixture was stirred for 16 h at room temperature. The reaction was quenched with saturated NH4Cl solution and diluted with H2O followed by the extraction with EtOAc (100 ml). The organic layer was separated, dried over MgSO4, filtered and the filtrate was evaporated to dryness and the residue was purified by FCC (SiO2, hexane/EtOAc) to give the product (0.11 g, 60%), as creamy paste. 1H-NMR (CDCl3) 7.66 (d, 2H, J=8.43 Hz); 7.51 (d, 2H, J=8.43 Hz); 3.81 (b, 2H); 3.01-2.86 (m, 2H); 2.71-2.67 (m, 4H); 2.50-2.10 (m, 2H); 1.94-1.82 (m, 5H); 1.52-1.48 (m, 1H); 1.18 (s, 3H); 1.02 (s, 3H).

Aufarbeitung

  1. customwas degassed with N2 and Cl2Pd(PPh3)2 (0.07 g)
  2. additionwas added
  3. customThe reaction was quenched with saturated NH4Cl solution
  4. additiondiluted with H2O
  5. extractionfollowed by the extraction with EtOAc (100 ml)
  6. customThe organic layer was separated
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customthe filtrate was evaporated to dryness
  10. customthe residue was purified by FCC (SiO2, hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-1f3978bcb4c44c27b7d862273c118d6b
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592399B2

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