Pyridine → HCID 66918652, compound

Participants

Reaction Conditions

Reaction Steps

(1S,2R,4S) and (1R,2S,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-isopropoxy-cyclopentanol (510 mg, 1.28 mmol) was dissolved in DCM (12 ml) and pyridine was added (206 μl, 2.56 mmol). The mixture was cooled to −35° C. and a solution of trifluoromethanesulfonic anhydride (253 μl, 1.54 mmol) in DCM (3 ml) was added. After the reaction mixture had been stirred for 5 h at −20° C. it was concentrated and passed trough a short plug of silica gel and then evaporated to dryness. The remaining oil was dissolved in THF (12 ml) and a solution of tertrabutylammonium cyanide in THF (3 ml) was added dropwise at −45° C. The reaction mixture was stirred at room temperature over night and then evaporated. The remaining yellow oil was purified by silica column chromatography (heptane/EtOAc 9:1) to obtain the title compound (311 mg, 60%) as colorless oil. MS (EI): 408.4 (M+H)+.

Provenance & Evidence