Hydrochloric Acid → HCID 21938699, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 8 (55 mg, 0.112 mmol) in THF (0.51 mL) was added 1.0 M BH3-THF (340 μL, 0.340 mmol) and the reaction heated to 50° C. for 22 hours. The reaction temperature was then increased to 80° C. and the reaction allowed to continue for an additional 24 hours. After cooling to room temperature, 2 M aqueous HCl (approx. 1 mL) was added to the reaction and the solution allowed to stir for one and one half hours. Next, the solution was basified with aqueous 2 M NaOH and extracted with DCM. The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. The resulting residue was then purified by flash column chromatography using silica gel and a gradient of 2 to 5% 2.0 M NH3 in EtOH/DCM to provide pure 9 (15 mg, 28%). LRMS calculated for C26H35F3N4O 476.28. Found 476.03.

Provenance & Evidence