Hydrochloric Acid → HCID 57038928, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of the methyl ester from Example 9, Step B (1.2 mmol, 330 mg) in 10 mL of DCM cooled to −78° C. was added dropwise over 20 min. diisobutylaluminum hydride (2.4 mmol, 2.4 mL of 1 M solution in DCM). The solution was stirred at −78° C. for 2 h. Methanol (2 mL) cooled to −78° C. was canulated dropwise to the reaction mixture over 5 min. After 10 min. the reaction was allowed to warm to room temperature, during which time a white precipitate formed. DCM (30 mL) was added, and the solution was poured into 2 N HCl (50 mL). The organic phase was collected and the aqueous phase was extracted with DCM (2×25 mL). The combined organic phase was dried with MgSO4 and the solvent removed under reduced pressure. The oily residue was dissolved in DCM and passed through a silica plug eluting with DCM. Removal of solvent under reduced pressure afforded the title compound as a clear oil. MS(ESI): m/z 250 (M+H). HPLC B: 1.31 min.

Provenance & Evidence