(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(2-oxopent-3-enyl)carbamate → (S)-Tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(2-oxopent-3-enyl)carbamate	HCID 131735280	—
Catalyst	(1,3-Bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene)(dichloro)((2-((propan-2-yl)oxy)phenyl)methylidene)ruthenium	HCID 11763533	—
Solvent	Toluene	HCID 1140	—
Product	(S)-Tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate	HCID 89852524	70.7%

Reaction Conditions

Temperature	65 °C

Reaction Steps

(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(2-oxopent-3-enyl)carbamate (Intermediate 49, 27.0 g, 70.39 mmol) was dissolved in toluene (650 ml). The solution was purged with nitrogen for 15 minutes before the addition of Hoveyda-Grubbs Catalyst 2nd Generation (0.885 g, 1.41 mmol). The reaction mixture was heated under nitrogen at 65° C. After 2 hours LCMS showed complete formation of the product. The reaction mixture was concentrated under reduced pressure. Silica gel chromatography (10%-35% ethyl acetate/hexanes) afforded the desired product as a solid (17.0 g, 70%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09309245B2
Source dataset	uspto-grants-2016_04
ORD ID	ord-7e104608dace4da3b1cc22f68a8745ba
Source note	uspto-grants-2016_04