Hydrochloric Acid → HCID 11383098, compound

Participants

Reaction Steps

To a solution of the title compound provided by Example 12 (25 mg, 0.068 mmol) in tetrahydofuran (5 ml) and methanol (10 ml) was added sodium borohydride (20 mg, 0.53 mmol). After stirring for 1.5 hours, the mixture was treated with water (10 ml) and hydrochloric acid (1 M, 0.6 ml). The mixture was concentrated to a volume of 8 ml and the solid was collected by filtration. The solid was treated with aqueous sodium carbonate solution (10%, 10 ml) and extracted with ethyl acetate (3×30 ml). The combined extracts were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography eluting with methanol-dichloromethane (5:95) to give the title compound (10 mg, 39% yield). 1H NMR (acetone-d6) δ1.36 (t, 3H, J=6.9 Hz, CH3), 3.95 (bs, 1H, OH), 4.09 (q, 2H, J=7.0 Hz, CH2), 4.56 (s, 2H, CH2), 5.28 (bs, 2H, NH2), 6.16 (d, 1H, J=1.1 Hz, Ar), 6.34 (d, 1H, J=1.1 Hz, Ar), 7.09 (d, 1H, J=8.5 Hz, Ar), 7.24 (d, 2H, J=8.8 Hz, Ar), 7.30–7.34 (m, 2H, Ar), 7.60–7.63 (m, 2H, Ar), 7.80 (s, 1H, NH).

Provenance & Evidence