Toluene → HCID 59732263, compound

Participants

Reaction Steps

To a stirred solution of 4-hydroxypiperidine (2.02 g, 20.0 mmol) and tert-butyl 4-oxopiperidine-1-carboxylate (3.99 g, 20.0 mmol) in 1,2-dichloroethane (50 mL) was added titanium isopropoxide (4.6 mL, 22.0 mmol) and the mixture was stirred for 18 h at room temperature. A solution of diethylaluminum cyanide in toluene (1M, 48.0 mL, 48.0 mmol) was added and stirred at room temperature for 24 h. Diluted with EtOAc and the reaction was quenched at 0° C. with saturated NaHCO3 (20 mL). The mixture was stirred a further 2 h, filtered through Celite, and the resulting filtrate was concentrated in vacuo to afford the title compound (5.89 g, 95%) as white solid, which was used for the next step without further purification.

Provenance & Evidence