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

Participants

Reaction Conditions

Reaction Steps

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]+.

Provenance & Evidence