Trifluoroacetic acid → HCID 23512244, compound

Participants

Reaction Steps

To a stirred mixture of methyl 3-(N,N-dimethylamino)-4-hydroxybenzoate (0.817 g, 4.18 mmol), N-tert-butoxycarbonylprolinol (0.926 g, 4.60 mmol), Ph3P (1.21 g, 4.60 mmol) in THF (20 mL) was added dropwise DIAD (95%) (0.953 mL, 4.60 mmol) at 0° C. The resulting mixture was heated under reflux for 41 hr. After cooling, the mixture was evaporated off in vacuo. The residue was chromatographed on silica-gel with EtOAc-n-hexane (1:10 to 1:6, v/v) as eluent to give a syrup which was used for the subsequent reaction without further purification. This syrup was dissolved in CH2Cl2 (10 mL) and added TFA (10 mL). After the solution was stirred for 5 hr at room temp, the solution was evaporated in vacuo. Water was added to the residue and washed with CHCl3. The aqueous layer was neutralized by the addition of sat. NaHCO3 and extracted with CHCl3. The extract was dried over Na2SO4 and evaporated in vacuo to afford 1.03 g (89%) methyl 3-(N,N-dimethylamino)-4-(2-pyrrolidinylmethoxy)benzoate as a gum.

Provenance & Evidence