Water → HCID 57904997, compound

Participants

Reaction Conditions

Reaction Steps

To benzyl (3-((tert-butyldimethylsilyloxy)methyl)cyclopentyl)(cyano)methyl(methyl)-carbamate (2.0 g, 4.80 mmol) in dry THF (40 mL) cooled to 0° C. was added tetrabutyl-ammoniumfluoride (1M in THF 17.28 mL). The reaction mixture was stirred at 23° C. for 5 hours. H2O (20 mL) was added to the reaction mixture and the organic material extracted with ethyl acetate (3×30 mL). The combined organic fractions were dried (MgSO4) and concentrated in vacuo. The crude material was purified on a Silica gel column (Biotage flash chromatography system), eluted with a gradient of ethyl acetate:hexane (3:7) to ethyl acetate 100% to afford 0.550 g (38% yield) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 7.39 (5 H, m), 5.13-5.25 (2 H, m), 5.07 (1 H, br s), 3.50-3.60 (2 H, m), 3.01 (3 H, s), 1.30-2.52 (8 H, m). LCMS (+ESI, M+H+) m/z 303.

Provenance & Evidence