tert-Butyl 4-(acetylthio)piperidine-1-carboxylate → HCID 178502577, compound

Participants

Reaction Conditions

Reaction Steps

Intermediate 6 (0.50 g) and Intermediate 12 (0.46 g) were combined in anhydrous methanol, degassed, cooled to −10° C., and treated with sodium bis(trimethylsilyl)amide (1.78 ml, as a 1.0 M solution in tetrahydrofuran), and the mixture stirred for 18 h, slowly warming to room temperature. The reaction was then reduced in vacuo, diluted with water (20 ml) and extracted with ethyl acetate (2×20 ml). The combined organic extracts were washed with aqueous 2% citric acid (20 ml), water (20 ml), saturated sodium bicarbonate (20 ml), saturated brine (20 ml), dried (Na2SO4) and solvents removed in vacuo to leave a straw coloured oil. This crude product was the purified by silica gel column chromatography, eluting with a gradient of 2% diethyl ether in dichloromethane rising to 4% diethyl ether in dichloromethane, to furnish the title compound as a colourless oil (0.29 g, 44%).

Provenance & Evidence