Carbon tetrabromide → Tert-butyl 3-(3,3-dibromoprop-2-en-1-yl)pyrrolidine-1-carboxylate

Temperatur

0 °C

A flask was charged with triphenylphosphine (477 g, 1.82 mol) and dichloromethane (2,500 ml) was cooled to 0° C. A solution of carbon tetrabromide (302 g, 910 mmol) in dichloromethane (300 ml) was added dropwise, followed by the dropwise addition of a solution of tert-butyl 3-(2-oxoethyl)pyrrolidine-1-carboxylate (97 g, 455.40 mmol, 1.00 equiv) in dichloromethane (200 ml). The resulting solution was allowed stir for 1.5 hours at 0° C. The reaction mixture was washed with 4,000 ml of petroleum ether, and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether gradient) to afford tert-butyl 3-(3,3-dibromoprop-2-en-1-yl)pyrrolidine-1-carboxylate as light yellow oil.

1. washThe reaction mixture was washed with 4,000 ml of petroleum ether
2. filtrationfiltered
3. concentrationThe filtrate was concentrated
4. customthe residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether gradient)

ORD-Eintrag

ord-de9ba585e96e469a85df97ff22abb0ff

Quelldatensatz

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08455477B2