Ethyl Acetate → (R)-2-(N-Boc-N-methylamino)-1-(tert-butyldimethylsilyloxy)-but-3-yne

HRID 1069761Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1069761
[C:1]([NH:8][C@H:9]([C:19]#[CH:20])[CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[Na+].[CH3:23]COC(C)=O>C1COCC1>[C:1]([N:8]([C@H:9]([C:19]#[CH:20])[CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH3:23])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 21971750(R)-N-Boc-2-amino-1-(-tert-butyldimethylsilyloxy)-but-3-yne

Produkt 1

HCID 21971749(R)-2-(N-Boc-N-methylamino)-1-(tert-butyldimethylsilyloxy)-but-3-yne

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(R)-2-(N-Boc-N-methylamino)-1-(tert-butyldimethylsilyloxy)-but-3-yne was synthesized according to Method Y above by the treatment of (R)-N-Boc-2-amino-1-(-tert-butyldimethylsilyloxy)-but-3-yne (200 mg, 0.67 mmol) (Example 104B) with NaH (21 mg, 0.87 mmol) and Mel (189 mg, 1.34 mmol) in THF (12 mL). The product was obtained after silica gel column chromatography with a 0-10% EtOAc in hexanes gradient. (Yield 200 mg, 95%).

Quellen und Nachweise

ORD-Eintrag
ord-32252ee2810c40c09604fde78338c342
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06252086B1

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