Acetic Acid → HCID 89585232, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, 0.5 g (1.69 mmol) of tert-butyl (S)-3-(thiazole-2-carbonyl)-piperidine-1-carboxylate were dissolved in 20 ml of tetrahydrofuran, and 3.374 ml (3.374 mmol) of lithium tri-sec-butylborohydride (1.0 M solution in tetrahydrofuran) were subsequently added dropwise at room temperature. After 60 minutes, 20 ml of acetic acid (10%) were added. Water, saturated sodium chloride solution and ethyl acetate were then added successively. The organic phase was separated off, the aqueous phase was post-extracted with ethyl acetate, and the combined organic phases were subsequently dried over sodium sulfate, filtered off and evaporated, giving 0.5 g of tert-butyl (S)-3-(hydroxythiazol-2-yl-methyl)piperidine-1-carboxylate as diastereomer mixture of the S-piperidine in the ratio 70:30 (polar:nonpolar); HPLC/MS (M+H)+=299.

Provenance & Evidence