Thiazole → HCID 71183822, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, 1.25 ml (17.62 mmol) of thiazole were dissolved in 20 ml of tetrahydrofuran at −70° C. 11.1 ml (17.62 mmol) [15% in n-hexane] were subsequently added dropwise at such a rate that the temperature did not exceed −67° C. The mixture was warmed to room temperature, then cooled to −70° C., and 3.76 g (17.62 mmol) of tert-butyl 3-formylpiperidine-1-carboxylate, dissolved in 5 ml of tetrahydrofuran, were added dropwise. The mixture was stirred at −70° C. for 1 h, warmed to room temperature and stirred for a further 2 h. Conventional work-up gave 5.18 g of tert-butyl 3-(hydroxythiazol-2-ylmethyl)-piperidine-1-carboxylate; HPLC/MS (M+H)+=299 as oil.

Provenance & Evidence