2-trimethylsilylethyl 4-oxopiperidine-1-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A slurry of 10% palladium on carbon (200 mg) in water was added to 4-oxo-piperidine-1-carboxylic acid-2-trimethylsilanyl-ethyl ester (2.42 g, 10 mmol) in 100 mL of methanol. Ammonium formate (6.0 g, 95 mmol) in water was added dropwise, and the mixture stirred vigorously overnight. The mixture was filtered and the filtrate concentrated in vacuo to leave the crude product. Chromatography (elution with methanol-dichloromethane) provided 0.98 g of product. The mixture was filtered the filtrate concentrated in vacuo to leave the crude product Chromatography (elution with methanol-dichloromethane)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Carbonic acid 4-nitro-phenyl ester-2-trimethylsilanyl-ethyl ester (8.33 g, 29.3 mmol), triethylamine (12.3 g, 122 mmol) and DMAP (3.6 g, 29.5 mmol) were added to a room temperature solution of 4-piperidone hydrochloride (4.52 g, 33.4 mmol) in 100 mL of acetonitrile. The resulting mixture was heated at reflux for 2 h, then cooled and the volatiles were removed in vacuo. The residue was dissolved in dichloromethane, washed with water and 1M NaOH solution, and concentrated in vacuo to leave 6.3 g of product. The resulting mixture was heated at reflux for 2 h cooled the volatiles were removed in vacuo The residue was dissolved in dichloromethane washed with water and 1M NaOH solution concentrated in vacuo