Water → HCID 69241992, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 17B (16.55 g, 44 mmol) in dry DMF (100 mL) under nitrogen was added tetrabutylammonium cyanide (50 g, 200 mmol). The mixture was heated to 50° C. for 60 hours and then poured into cold water and extracted with ethyl acetate (3×250 mL). The combined organic layers were dried (magnesium sulfate) and concentrated under reduced pressure. The residue was purified by flash silica gel chromatography with 50% ethyl acetate/50% hexane to provide the titled compound (12 g). MS (ESI) m/e 312 (M+H)+, 310 (M−H)−; 1H NMR (400 MHz, CD3OD) δ ppm 1.44 (m, 9 H) 2.10 (m, 1 H) 2.79 (m, 1 H) 3.05 (m, 1 H) 3.17 (m, 1 H) 3.33 (m, 1 H) 3.57 (dd, 1 H) 3.83 (m, 2 H) 3.96 (m, 1 H) 4.48 (m, 1 H) 4.65 (m, 2 H).

Provenance & Evidence