Chlorotrimethylsilane → Benzyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate

https://huagongshe.com/reaction/2035643

Participants

Role	Name	HCID	Charge
Reactant	Chlorotrimethylsilane	HCID 6397	—
Reactant	Triethylamine	HCID 8471	—
Reactant	Benzyl 4-oxopiperidine-1-carboxylate	HCID 643496	—
Solvent	Dimethylformamide	HCID 6228	—
Product	Benzyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate	HCID 57502431	557.3%

Reaction Conditions

Temperature	80 °C

Reaction Steps

To benzyl 4-oxopiperidine-1-carboxylate (152 g, 650 mmol) in DMF (650 mL) was added TMS-Cl (148 mL, 117 mmol) followed by triethylamine (326 mL, 234 mmol). The slurry was warmed to 80° C. for 16 hours, diluted with hexanes (1 L), washed 3 times with saturated NaHCO3 solution, dried over Na2SO4, filtered and concentrated to obtain benzyl 4-(trimethylsilyloxy)-5,6-dihydropyridine-1(2H)-carboxylate, (199 g, 652 mmol) as a orange oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08575145B2
Source dataset	uspto-grants-2013_11
ORD ID	ord-2289ca4aaa8f4662adf61493ebf7cb44
Source note	uspto-grants-2013_11