Borane → HCID 10297313, compound

Participants

Reaction Steps

A solution of the 3-[(3R)-3-methoxy-1-azabicyclo[2.2.2]oct-3-yl]-1,1-di(2-thienyl)-2-propyn-1-ol compound complexed with borane 193 (200 mg, 0.54 mmol) in THF (10 ml) under nitrogen and at room temperature was treated with NaH (60% dispersion in oil, 23 mg, 0.59 mmol). After 20 minutes, methyl bromoacetate (55 μL, 0.59 mmol) was added in one portion. After 16 hours, the reaction was quenched with water, and the mixture was then diluted with AcOEt. The organic phase was washed with brine, dried over MgSO4 and evaporated to dryness to afford the methyl {[3-[(3R)-3-methoxy-1-azabicyclo[2.2.2]oct-3-yl]-1,1-di(2-thienyl)-2-propynyl]oxy}acetate compound complexed with borane (1:1) 194 as an oil (130 mg, 55%). This compound was used without other purification in the next step.

Provenance & Evidence