tert-Butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate → HCID 67315283, compound

Participants

Reaction Steps

To a solution of 4-methoxybenzothiazole (413 mg, 2.5 mmol) in THF (10 ml) at −75° C. was added dropwise n-BuLi (2.5M in Hex, 1.1 ml) such that the temperature did not exceed −70° C. The brown solution was stirred at this temperature for 15 min before the dropwise addition of a solution of 4-(methoxy-methyl-carbamoyl)-piperidine-1-carboxylic acid tert-butyl ester (680 mg, 2.5 mmol) in THF (2 ml). The temperature was also kept below −70° C. The brown solution was then gradually allowed to reach RT (over 3 h). The mixture was poured on water and extracted with EtOAc. Organic extracts were washed with brine and dried over MgSO4 and concentrated. Chromatography on SiO2 (hex/EtOAc 2:1) gave 565 mg (60%) of a yellowish solid.

Provenance & Evidence