Tetrahydro-4H-pyran-4-one → [2-(Tert-butyl-dimethylsilanyloxy)-ethyl]-(tetrahydro-pyran-4-yl)-amine

Participants

Reaction Steps

To a stirred cooled solution of tetrahydro-pyran-4-one (2 g, 19.98 mmol) in methanol (30 mL) were added 2-(tert-butyl-dimethylsilanyloxy)-ethylamine (8c) (2.5 mg, 13.98 mmol). Stirring was continued for 1 h at room temperature. The reaction mixture was cooled and Na(CN)BH3 (2.5 g, 39.96 mmol) was added portion-wise, followed by stirring at room temperature for 20 h. The reaction mixture was quenched with water and the methanol was removed. The mixture was subsequently extracted with dichloromethane (3×30 mL) and the organic part was concentrated, dried and purified by Combi-Flash column (eluted at 20-50% ethyl acetate in hexane) to get [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-(tetrahydro-pyran-4-yl)-amine (8j) (2.5 g, 48.23 mmol) as a light yellow oil.

Provenance & Evidence