Hydrochloric Acid → HCID 64222602, compound

Participants

Reaction Conditions

Reaction Steps

To a dried flask under nitrogen was added borane tetrahydrofuran complex (1 M solution, 8.79 ml, 8.79 mmol), and tetrahydrofuran (10 ml). The solution was cooled to 0° C. and a solution of 5-methyl-5-(2-pyridinyl)-2-piperidone (Preparation 41, 1 g, 5.26 mmol) in tetrahydrofuran (20 ml) was added. The reactants were warmed to room temperature and then heated at reflux for 6 h. Further borane tetrahydrofuran, complex (1M solution, 8.79 ml, 8.79 mmol) was added and the reaction mixture was heated at reflux for 18 h. Thin layer chromatography still showed starting material was present so further borane tetrahydrofuran complex (1M solution, 8.79 ml, 8.79 mmol) was added and the reaction mixture was heated under reflux for 18 h. Upon completion hydrochloric acid (6M) was added to the reaction mixture and the mixture was stirred for 30 min. The reaction mixture was partially concentrated before adjusting to pH 11 with solid sodium hydroxide. The organic extracts were extracted with dichloromethane (5×20 ml) and dried (Na2SO4) to give a crude oil (0.45 g). The oil was purified by flash chromatography eluting with dichloromethane:methanol:0.88 ammonia solution (94:4:2) to give the title compound as an oil (0.20 g, 22%).

Provenance & Evidence