Acetic Acid → HCID 69491155, compound

Participants

Reaction Steps

Acetic acid (0.007 mL, 0.12 mmol) and sodium triacetoxyborohydride (42 mg, 0.20 mmol) were added to a suspension of compound 1g (50 mg, 0.13 mmol) and acetone (0.010 mL, 0.14 mmol) in DCE (0.5 mL). The reaction was stirred at rt for 16 h. Trimethylorthoformate (0.5 mL) was added, and the reaction was stirred at rt for 24 h. MeOH (1 mL) was added, and the reaction was stirred for 3 h. The reaction mixture was concentrated on a rotary evaporator and the residue was purified by preparative tlc (silica gel, 9:1 chloroform/methanol). This material was dissolved in a mixture of MeOH (3 mL) and TEA (0.040 mL, 0.29 mmol), and Raney nickel (washed with methanol) was added. The reaction mixture was hydrogenated overnight (50 psi), filtered, and concentrated on a rotary evaporator. The residue was purified by reverse phase HPLC (C18 column, water/acetonitrile gradient containing 0.1% TFA) to give to give Example 11. ESI-MS m/e 385.4 (M+1).

Provenance & Evidence