Triethylsilane → HCID 117690149, compound

Participants

Reaction Steps

(S)-tert-butyl 3-(hydroxymethyl)-4-(2-(3-nitrophenyl)-2-oxoethyl)piperazine-1-carboxylate (1.5 g, 3.95 mmol) was dissolved in mixture of DCM (10 mL)/TFA (5 ml) then added triethylsilane (3.16 mL, 19.8 mmol) and stirred at room temperature overnight. The reaction mixture was concentrated. The residue was dissolved in DCM (15 mL) with saturated aqueous NaHCO3 (15 ml) and di-tert-butyl dicarbonate (2.157 g, 9.88 mmol) was added then stirred for 2 hrs. The reaction was extracted with DCM (2×). The combined DCM was washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The product was chromatographed through 120 g ISCO Redi-sep column and eluted with 10-70% ethyl acetate/hexane to yield the title compound; the product was almost exclusively the trans isomer.

Provenance & Evidence