1-Bromo-3-chloropropane → 5-(3-chloropropyl)hexahydro-1H-furo[3,4-c]pyrrole

To a solution of hexahydro-1H-furo[3,4-c]pyrrole (0.15 g) in acetone (50 mL) was added K2CO3 (0.46 g) and 1-chloro-3-bromopropane (0.42 g, 2.0 eq) in turn. The reaction mixture was heated to reflux for 12 h and filtered. The filtrate was concentrated in vacuo and the residue was dissolved in EtOAc (100 mL). The solution was washed with water twice followed by brine once. The solution was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was chromatographed with a silica gel column (eluting agent: 20:1 (v/v) EA/CH3OH) to give the title compound (0.13 g, 50.04%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 190.7 (M+1).

1. temperatureThe reaction mixture was heated
2. temperatureto reflux for 12 h
3. filtrationfiltered
4. concentrationThe filtrate was concentrated in vacuo
5. dissolutionthe residue was dissolved in EtOAc (100 mL)
6. washThe solution was washed with water
7. dry with materialThe solution was dried over anhydrous Na2SO4
8. concentrationconcentrated in vacuo
9. customThe residue was chromatographed with a silica gel column (eluting agent: 20:1 (v/v) EA/CH3OH)

ORD record

ord-0d551476c236425b80423284da40c02b

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181277B2