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

Temperature

55 °C

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%).

1. temperatureThe reaction mixture was cooled to room temperature
2. extractionextracted with EtOAc (50 mL)
3. customThe organic phase was separated from the mixture
4. extractionthe water phase was extracted with EtOAc (20 mL×3)
5. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
6. filtrationfiltered
7. concentrationThe filtrate was concentrated in vacuo
8. customthe residue was purified with a silica gel column chromatography (1:1 (v/v) PE/EtOAc)

ORD record

ord-ccfc29f4a40a497d81988184f3b7b7cd

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181277B2