反应详情

To a solution of 5-Nitro-m-xylene-α,α′-diol (890 mg, 5.4 mmol) in methanol (50 mL) was added Pd/C (10%, 287 mg). A hydrogen atmosphere was introduced and the mixture was hydrogenated under pressure (H2, 5˜8 psi) for 5 hours at room temperature. The solution was filtered through celite and the filtrate was evaporated by rotary evaporation in vacuo to give 5-amino-m-xylene-α,α′-diol, which was then dissolved in THF (10 mL)/DMF (15 ml). 4-methyldithio-4,4-dimethyl butanoic acid (1.05 g, 5.4 mmol) dissolved in THF (5 ml) was added at room temperature followed by the addition of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.1 g, 10.8 mmol) and 4-dimethylamino pyridine (66 mg, 0.54 mmol). The obtained mixture was stirred at room temperature overnight then quenched with 10% ammonium chloride, extracted with ethylacetate, washed and dried. It was filtered and the solvents were removed by rotary evaporation in vacuo. The residue was purified by flash chromatography (CH2Cl2/MeOH, 15:1, 10:1, 7:1) to furnish 5-(N-4-methyldithio-4,4-dimethylbutanoyl)-amino-1,3-bis-(hydroxymethyl)-benzene as a white solid (729 mg).

1. filtrationThe solution was filtered through celite
2. customthe filtrate was evaporated by rotary evaporation in vacuo