Potassium Carbonate → HCID 86607622, compound

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Reaction Steps

tert-Butyl-4-bromobutyrate (10 mmol) in DMF (100 mL) was treated with dibenzyl malonate (20 mmol) and potassium carbonate (30 mmol) at 40° C. overnight. EtOAc (200 mL) and saturated aqueous ammonium chloride (100 mL) were added and the separated organic layer was washed with 1N HCl (50 mL), saturated aqueous ammonium chloride (100 mL), brine (100 mL), and water (100 mL). After removal of the solvent in vacuo, the crude product was dissolved in dichloromethane (60 mL) and treated at room temperature with trifluoroacetic acid (15 mL) for 2 h. Removal of the solvent in vacuo afforded the crude product, which was purified by reverse phase preparative HPLC using 0.05% TFA/CH3CN/H2O as the mobile phase. The title compound (37) (2 g) was obtained as a colorless oil. 1H NMR (CD3OD, 400 MHz): δ 7.3 (m, 10H), 5.1 (q, 4H), 3.5 (t, 1H), 2.3 (t, 2H), 1.9 (q, 2H), 1.6 (m, 2H). MS (ESI) m/z 370.4 (M+H)+.

Provenance & Evidence