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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 585494Generated: October 30, 2026

Dimethylformamide → tert-Butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate

https://huagongshe.com/reaction/585494

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantChlorotrimethylsilaneHCID 6397—
ReactantTriethylamineHCID 8471—
Reactanttert-Butyl 2-oxopiperidine-1-carboxylateHCID 7577838—
Producttert-Butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylateHCID 1077854062%

Reaction Conditions

Temperature70 °C

Reaction Steps

Trimethylsilyl chloride (25 ml) and triethylamine (50 ml) were added to a stirred solution of N-Boc piperidinone (30 g) in DMF (40 ml) and the mixture was heated at 70° C. for 16 h. The solution was cooled to room temperature and diluted with hexanes (300 ml), the solution was washed with sodium bicarbonate solution (3×100 ml), dried (MgSO4) and evaporated to give a colourless oil. The product was purified on silica eluting with 10% ethyl acetate/hexanes to give the title compound as colourless oil (25 g, 62%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06933306B2
Source datasetuspto-grants-2005_08
ORD IDord-e52d715d22e545cea3d7daa7b3c1f38e
Source noteuspto-grants-2005_08