Tetrahydrofuran → 1-Benzyl-3-(2-tert-butyldimethylsiloxy-1-hydroxyethyl)-4-piperidinone

Participants

Reaction Conditions

Reaction Steps

The above N-(1-benzyl-4-piperidylidene)cyclohexylamine (4.81 g (17.69 mmol)) was dissolved in 150 ml of tetrahydrofuran. After this solution was cooled to -78° C., 13.3 ml (21.2 mmol) of 1.6 M n-butyl lithium in hexane was added dropwise. After the reaction mixture was stirred for 30 minutes under ice-cooling, a solution of 4.01 g (23.0 mmol) of tert-butyldimethylsiloxyacetaldehyde in 50 ml of tetrahydrofuran was added, followed by stirring for 1 hour under ice-cooling. To the reaction mixture, aqueous ammonium chloride was added, followed by stirring for 10 minutes and 3 extractions with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to yield 1-benzyl-3-(2-tert-butyldimethylsiloxy-1-hydroxyethyl)-4-piperidinone.

Provenance & Evidence