Acetic Acid → HCID 54000860, compound

Participants

Reaction Conditions

Reaction Steps

The product from Example 11 (2.0 g, 8.2 mmol) can be added to a solution of borane dimethylsulfide complex (2.5 g, 33 mmol) in 25 ml of dry tetrahydrofuran at room temperature. After one hour, the mixture can be heated to reflux for 4 hours under nitrogen. The resulting suspension can then be cooled to 0° C., cautiously treated dropwise with 5 ml of glacial acetic acid and, after hydrogen evolution ceases, the solution can be heated to reflux for 8 hours. The mixture can then be cooled to 0° C., cautiously treated with water and concentrated in vacuo. The aqueous residue can be extracted with ether, basified with 10 N sodium hydroxide and reextracted with methylene chloride-ethanol. The methylene chloride extracts can then be combined, dried (Na2SO4), filtered and concentrated in vacuo to give the crude product. The pure title compound can be obtained by chromatography on silica gel with 20% methanol in chloroform.

Provenance & Evidence