Diisobutylaluminumhydride → HCID 57937448, compound

Participants

Reaction Conditions

Reaction Steps

1,1-Dimethylethyl 4-[(2-acetyl-4-pyridinyl)oxy]-1-piperidinecarboxylate (1.62 g, 5.06 mmol) was dissolved in 50.0 mL of anhydrous DCM and the solution cooled to −78° C. Diisobutylaluminumhydride (15.2 ml, 15.2 mmol, 1.0M solution in hexanes) was added dropwise over 15 min and the reaction continued to be stirred at −78° C. for 1.5 h. The reaction was quenched with 50 mL of saturated sodium potassium tartrate solution, warmed to rt and stirred overnight. The organics were separated, washed with brine and dried over MgSO4. The crude was purified via silica gel chromatography to give 0.962 g (59% yield) of the title compound, 1H NMR (300 MHz, Chloroform-d) δ 8.40 (d, J=5.8 Hz, 1H), 6.83 (d, J=2.4 Hz, 1H), 6.77 (dd, J=5.8, 2.4 Hz, 1H), 4.82-4.97 (m, J=6.5, 6.5 Hz, 1H), 4.51-4.74 (m, 1H), 3.62-3.83 (m, 2H), 3.29-3.53 (m, 2H), 1.90-2.08 (m, 2H), 1.66-1.90 (m, 2H), 1.55 (d, J=6.5 Hz, 3H), 1.52 (s, 9H).

Provenance & Evidence