HCID 20781251, compound → HCID 20781265, compound

Participants

Reaction Steps

LiAlH4 (0.29 ml of 1M solution in tetrahydrofuran, 0.29 mmol) in tetrahydrofuran (3 ml) at 0° C. under nitrogen was treated dropwise with a solution of the ester of Example 38 (50 mg, 0.1 mmol) in tetrahydrofuran (9 ml). The reaction mixture was stirred at ambient temperature for 3 days, quenched with aqueous sodium sulfate then partitioned between water and ethyl acetate. The combined organic layers were dried (MgSO4) and evaporated to give a residue (47 mg) which was purified using preparative thin layer chromatography eluting with ethyl acetate:hexane 2:1 to give the desired product (12 mg). 1H NMR (CDCl3) 7.38 (2H, d, J=9.2 Hz), 7.32 (2H, d, J=8.8 Hz), 7.08-7.04 (2H, m), 6.88-6.84 (1H, m), 5.39 (1H, d, J=6.4 Hz), 4.51-4.09 (2H, m), 3.65-3.63 (1H, m), 3.28 (2H, t, J=5.2 Hz), 2.83 (1H, t, J=5.6 Hz), 2.56-2.44 (4H, m), 2.05-2.20 (2H, m), 1.57-1.50 (2H, m); M/z(ES−)=492/494

Provenance & Evidence