Sodium borohydride → HCID 178515596, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve 3-(2,4-dichloro-benzyl)-1-(4-oxo-cyclohexyl)-pyrrolidin-2-one (Example 14) (6.19 g, 18.19 mmol) in MeOH (200 mL) and cool to 0° C. under nitrogen. Add sodium borohydride (1.38 g, 36.39 mmol) and stir the solution at 0° C. for 4 hours. Add water (200 mL) and extract the aqueous layer with ethyl acetate (3×300 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 50-80% EtOAc-Hexane) to give 5.49 g (88%) of the title product as a white solid. 1H NMR (CDCl3) δ 7.37 (d, 1H), 7.22 (d, 1H), 7.17 (dd, 1H), 3.91-4.00 (m, 1H), 3.52-3.62 (m, 1H), 3.27-3.36 (m, 1H), 3.12-3.21 (m, 2H), 2.73-2.82 (m, 2H), 1.98-2.07 (m, 3H), 1.56-1.77 (m, 4H), 1.38-1.54 (m, 4H).

Provenance & Evidence