Tert-butyl 3-(3,3-dibromoprop-2-en-1-yl)pyrrolidine-1-carboxylate → 1207840-16-1

Temperature

-80 °C

A flask was charged with tert-butyl 3-(3,3-dibromoprop-2-en-1-yl)pyrrolidine-1-carboxylate (155 g, 420. mmol) and (1,800 ml) and cooled to −80° C. A solution of butyllithium (370 ml, 2.20 equiv) was added dropwise such that the internal temperature was maintained at −80° C. After stirring for an addition hour at −80° C., the reaction mixture was quenched by the addition of 1,000 mL of saturated aqueous ammonium chloride. The resulting mixture was extracted with diethyl ether (3×1,000 mL). The combined organic layers were washed with brine (3×800 mL), then dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether gradient) to afford tert-butyl 3-(prop-2-ynyl)pyrrolidine-1-carboxylate as light yellow oil.

1. temperaturewas maintained at −80° C
2. customthe reaction mixture was quenched by the addition of 1,000 mL of saturated aqueous ammonium chloride
3. extractionThe resulting mixture was extracted with diethyl ether (3×1,000 mL)
4. washThe combined organic layers were washed with brine (3×800 mL)
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether gradient)

ORD record

ord-619efb12e83c44398f992abdb159428c

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455477B2