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-2cd957f2209c49718a508244bff04d93

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09102676B2