Aluminium lithium hydride → HCID 56593709, compound

Participants

Reaction Steps

A solution of compound 115 (2.28 g, 6.563 mmol) in dry THF (30 mL) was treated with LiAlH4 (2.49 g, 65.636 mmol) portion wise over a period of 45 min. at 0° C. The reaction was brought to room temperature and stirred for 48 h. The reaction was quenched with sodium sulfate decahydrate (8.0 g) followed by careful addition of water (9 mL) at 0° C. and stirred for 30 min. at room temperature. The reaction was diluted with ethyl acetate (50 mL), filtered and washed with ethyl acetate (2×50 mL). The combined ethyl acetate layer was evaporated and crude was purified by column chromatography (2M NH3 in MeOH:CH2Cl2, 5:95 to 1:9) to obtain compound 116 (0.44 g, 22%) as a foam. 1H NMR (DMSO-d6) δ 1.76-1.87 (m, 1H), 2.11-2.23 (m, 1H), 2.27 (s, 3H), 2.36 (t, 1H, J=8.4 Hz), 2.42-2.48 (m, 1H), 2.64-2.71 (m, 1H), 2.90 (t, 1H, J=8.1 Hz), 3.37-3.45 (m, 1H), 4.26 (d, 2H, J=5.7 Hz), 5.88 (t, 1H, J=6.0 Hz), 6.34 (d, 1H, J=0.9 Hz), 6.45 (dd, 1H, J=1.8, 8.4 Hz), 6.72 (d, 1H, J=1.2 Hz), 7.17-7.38 (m, 6H), 10.11 (s, 1H); ESI-MS (m/z, %) 306 (MH+, 100); ESI-HRMS calculated for C20H24N3 (MH+), calculated: 306.1964, observed: 306.1967.

Provenance & Evidence