Acetic Acid → HCID 11379291, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of aniline (0.58 mL, 6.4 mmol) and acetic acid (0.73 mL, 12.8 mmol) in MeOH (6 mL) was added 1,4-dioxaspiro[4.5]decan-8-one (1.0 g, 6.4 mmol). The mixture was stirred at 50° C. for 2 h. Then, NaCNBH3 (402 mg, 6.4 mmol) was added at 0° C. The mixture was stirred at room temperature for 2 h. Then, 2 M aqueous NaOH was added to quench the reaction. The organic materials were extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4 and filtered. After removal of the solvent at reduced pressure, the residue was purified by column chromatography (Purif, silica gel, 95:5 hexane/EtOAc to 70:30 hexane/EtOAc) to give the crude title compound (1.39 g, 93%) as a pale yellow solid:

Provenance & Evidence