Lithium diisopropylamide → 2-(2-bicyclo[2.2.1]heptanylamino)-5-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-1,3-thiazol-4-one

HRID 852791

Reaktionsgleichung

Reaktionsgleichung von HRID 852791
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[S:10][C:11]([CH2:16][CH:17]2CCN(C(OC(C)(C)C)=O)CC2)(C)[C:12](=[O:14])[N:13]=1.C12CC(CC1)CC2NC1SCC(=O)N=1.C([N-]C(C)C)(C)C.[Li+].BrCC[O:55][Si:56]([C:59]([CH3:62])([CH3:61])[CH3:60])([CH3:58])[CH3:57]>>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[NH:8][C:9]1[S:10][CH:11]([CH2:16][CH2:17][O:55][Si:56]([C:59]([CH3:62])([CH3:61])[CH3:60])([CH3:58])[CH3:57])[C:12](=[O:14])[N:13]=1

Komponenten

5

Edukt 4

HCID 2724682Lithium diisopropylamideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 178451850tert-butyl 4-[[2-[[(2S)-2-bicyclo[2.2.1]heptanyl]amino]-5-methyl-4-oxo-1,3-thiazol-5-yl]methyl]piperidine-1-carboxylateHCID 178516936HCID 178516936, Verbindung

Produkt 1

HCID 1784552022-(2-bicyclo[2.2.1]heptanylamino)-5-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-1,3-thiazol-4-one

Versuchsvorschrift

The title compound was prepared according to the procedure described in the preparation of tert-butyl 4-((2-((2S)-bicyclo[2.2.1]heptan-2-ylamino)-5-methyl-4-oxo-4,5-dihydrothiazol-5-yl)methyl)piperidine-1-carboxylate by using 2-(bicyclo[2.2.1]heptan-2-ylamino)thiazol-4(5H)-one (1.00 g, 4.76 mmol), lithium diisopropylamide (Aldrich, 2.0 M in heptane/THF/ethylbenzene, 8.5 mL, 19.0 mmol), and (2-bromoethoxy)(tert-butyl)dimethylsilane (Aldrich, 6.83 g, 28.5 mmol). The title compound was obtained as an off-white solid (950 mg). MS (ESI, pos. ion) m/z: 369 (M+H).

Aufarbeitung

  1. customThe title compound was prepared

Quellen und Nachweise

ORD-Eintrag
ord-de2efd32337848d6a5f9a2d82273e8d9
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253196B2

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