Hydrochloric Acid → HCID 58695801, compound

Participants

Reaction Steps

To a solution of (S) (−)-α,α-dephenyl-2-pyrrolidinemethanol (0.724 g, 2.86 mmol) in anhydrous tetrahydrofuran (25 mL) was added trimethylborate (0.446 g, 4.29 mmol) all at once and stirred at room temperature for 1 h. The borane dimethylsulfide complex (7.15 mL, 14.3 mmol, 2.0 M in THF) was added dropwise over a period of 1 h. The mixture was then cooled to 0° C. with an ice-bath and a solution of ethyl 3-(4-chloro-2-propionylphenyl)-8-azabicyclo[3.2.1]octane-8-carboxylate (2-7) (5.00 g, 14.9 mmol) in 15 mL of anhydrous tetrahydrofuran was added dropwise over a period of 3 h (keeping the reaction temperature below 4° C.). The reaction mixture was allowed to warm slowly up to room temperature and stirred overnight. After the reaction was complete, the mixture was added portionwise to a stirring mixture of 2 N HCl (125 mL) and EtOAc (100 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered, and concentrated. Purification of the crude residue by flash chromatography over silica gel (5% ethyl acetone/dichloromethane as eluent) afforded (2-8) as a colorless oil.

Provenance & Evidence