Acetic Acid → HCID 91091752, compound

Participants

Reaction Conditions

Reaction Steps

A solution of Example 26B (1.2 g, 2.2 mmol) in methanol (7 mL) was treated with Pd(OH)2 (0.24 g), 4N HCl (0.54 mL), stirred under a hydrogen balloon at 25° C. for 16 hrs. The catalyst was filtered, washed with methanol, and the solvents were evaporated to give 1 g (100%) of the crude product used directly for the next step. This material (0.5 g, 1.1 mmol) was dissolved in dichloroethane (4 mL) and treated with acetic acid (0.12 mL, 2 equivalent), sodium triacetoxyborohydride (0.57 g, 2.5 equivalent), and p-anisaldehyde (0.26 mL, 2 equivalents) at 25° C. for 16 hrs. The mixture was quenched with 10% sodium bicarbonate and chloroform. The organic layer was separated, washed with brine, dried over sodium sulfate, filtered and the solvents were evaporated. The crude residue was purified using 1% methanol/chloroform to give 0.38 g (60%) of the title compound.

Provenance & Evidence