Methyl iodide → HCID 68569123, compound

Participants

Reaction Steps

To a solution of N-Boc-4-piperidone (Boc-29.155) (201 mg, 1.01 mmol) in THF (5 mL), cooled by dry ice/acetone, was added 2-thienyllithium (1M in THF, 1.5 mL, 1.5 mmol). After 50 min, the cooling bath was removed; after additional 1 h, methyl iodide (125 μL, 2.01 mmol) was added, and the solution was stirred at ambient temperature overnight. The solvent was evaporated, water was added, and the mixture was extracted with EtOAc (4×15 mL). The combined organic layers were washed with water and brine, dried over MgSO4, filtered and concentrated. The crude material (acc. to 1H NMR mixture of methyl ether and the alcohol in a 1:2 ratio) was methylated according to the general procedure, yielding 300 mg (1.01 mmol, 100% yield) of the title compound as yellow oil. 1H NMR (CDCl3, 200 MHz): δ=1.46 (s, 9H), 1.93 (brdt, J=4.3, 12.6 Hz, 2H), 2.00 (brd, J=12.8 Hz, 2H), 3.05 (s, 3H), 3.16 (brt, J=11.0 Hz, 2H), 3.84 (brd, J=12.2 Hz, 2H), 6.93-7.00 (m, 2H), 7.25-7.31 (m, 1H).

Provenance & Evidence