Diiodomethane → 1-Tert-butyl 3-ethyl 3-(iodomethyl)piperidine-1,3-dicarboxylate

Temperature

0 °C

A solution of diisopropylamine (14.6 mmol, 2.05 mL) in THF (15 mL) was cooled to −78° C. N-butyllithium (1.6 M in hexane) (16 mmol, 10 ml) was added dropwise and the solution was stirred for 30 minutes at 0° C. After cooling to −78° C. a solution of 1-tert-butyl 3-ethyl piperidine-1,3-dicarboxylate (14.6 mmol, 3.75 g) in 20 ml THF was added and the solution was stirred for 3 h at −78° C. A solution of diiodomethane (16 mmol, 1.3 mL) in THF (10 mL) was added and the solution was stirred for 2 days at room temperature. The reaction was quenched by the addition of water and extracted twice with EtOAc. The organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The crude was purified by flash chromatography (heptane/EtOAc: 10 to 50%) yielding the title compound (C1) (4.5 g, 74%). MS (ES) C14H24INO4 requires: 397. found: 420.1 [M+Na]+.

1. additionwas added
2. stirringthe solution was stirred for 3 h at −78° C
3. stirringthe solution was stirred for 2 days at room temperature
4. customThe reaction was quenched by the addition of water
5. extractionextracted twice with EtOAc
6. washThe organic layers were washed with brine
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe crude was purified by flash chromatography (heptane/EtOAc: 10 to 50%)

ORD record

ord-6c6fb1b058c54adcae23208f0c12a9d0

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772286B2