Water → HCID 53656255, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the product of Step 10 (10.1 g, 0.015 mol) and pyridinium p-toluenesulfonate (1.12 g, 0.045 mol) in a mixture of MeOH:THF 3:1 (80 mL) was warmed to 60° C. overnight. Most of the MeOH was evaporated and an aqueous solution of NH4Cl was added. The product was extracted with EtOAc, washed with brine and dried over Na2SO4. The residual oil was purified by flash chromatography on silica using 1:5 to 1:3 EtOAc:hexane. The product was then dissolved in a mixture of MeOH:THF, 3:1 (70 mL) and the solution was cooled down to 0° C. for the addition of a 1M solution of NaOH in water (35 mL, 0.036 mol). The reaction mixture was stirred 2 days at r.t. Most of the MeOH was evaporated and the solution was acidified with AcOH (acetic acid) to pH ≈5. An aqueous solution of NH4Cl was added and the acid was extracted with EtOAc. The organic phases were washed with brine and dried over Na2SO4. After evaporation of the solvent, the residual oil was purified by flash chromatography using 1:6 to 1:5 EtOAc:hexane (containing 2% AcOH) to give 7.6 g of the title product (87% yield).

Provenance & Evidence