1,2-Dichloroethane → benzyl tetrahydro-2H-[1,4]dioxino[2,3-c]pyrrole-6(3H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of NaOH aqueous solution (35 w/w %, 21 mL, aq.), ClCH2CH2Cl (21 mL), benzyl 3,4-dihydroxypyrrolidine-1-carboxylate (1.16 g, 4.9 mmol, 1.0 eq) and TBAB (0.31 g, 0.98 mmol, 0.2 eq) was heated at 55° C. for 48 h in a round-bottom flask. The reaction mixture was cooled to room temperature and poured into water (50 mL), extracted with EtOAc (50 mL). The organic phase was separated from the mixture, and the water phase was extracted with EtOAc (20 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified with a silica gel column chromatography (1:1 (v/v) PE/EtOAc) to give the product as colorless oil (0.50 g, 39%).

Provenance & Evidence