Sodium Carbonate → HCID 57905223, compound

Participants

Reaction Conditions

Reaction Steps

To 2-(3-((tert-butyldimethylsilyloxy)methyl)cyclopentyl)-2-(methylamino)acetonitrile (6.0 g, 21.24 mmol) in THF (33 mL), H2O (15 mL) was added, at 0, ° C. Na2CO3 (4.50 g, 42.48 mmol) followed by the dropwise addition of benzyl chloroformate (3.89 mL, 27.6 mmol) over 10 min. The reaction mixture was stirred at 0° C. for 30 min. then at 23° C. for 18 hours. H2O (150 mL) was then added and the organic material was extracted with ethyl acetate (3×100 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 (1:4) to (1:1) to afford 3.90 g (44% yield) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 7.34-7.45 (5 H, m), 5.33 (2 H, s), 5.18-5.25 (1H, m), 3.48-3.59 (2 H, m), 3.00 (3 H, s), 2.35-2.47 (2 H, m), 1.55-2.25 (6 H, m), 0.94 (9 H, s), 0.05 (6 H, s). LCMS (+ESI, M+H+) m/z 417.

Provenance & Evidence