Tert-butyl 4-(3,3-dibromoallyl)piperidine-1-carboxylate → Tert-butyl 4-(prop-2-yn-1-yl)piperidine-1-carboxylate

Temperature

-78 °C

To a solution of 118 mg (0.31 mmol) of 1-(t-butoxycarbonyl)-4-(3,3-dibromoprop-2-en-1-yl)piperidine from Step A in THF (4 mL) at −78° C. was added a 2.5M solution of n-butyl lithium (0.370 mL, 0.92 mmol). After stirring at −78° C. for 45 min, the reaction mixture was quenched with sat'd ammonium chloride (4 mL) and diluted with ether (25 mL). After separating the phases, the aqueous layer was extracted with ether. The combined organic phases were washed with brine, dried over magnesium sulfate and concentrated. The residue was purified by FC (4:1 v/v hexanes/ether) to give the title compound (55 mg).

1. customthe reaction mixture was quenched with sat'd ammonium chloride (4 mL)
2. additiondiluted with ether (25 mL)
3. customAfter separating the phases
4. extractionthe aqueous layer was extracted with ether
5. washThe combined organic phases were washed with brine
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated
8. customThe residue was purified by FC (4:1 v/v hexanes/ether)

ORD record

ord-dd214cf51dcc427d8f8b251ac61459f6

Source dataset

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06593346B2