Aluminium lithium hydride → HCID 67001538, compound

Participants

Reaction Steps

Solid LiAlH4 (357 mg, 9.41 mmol) was added to a vigorously stirred solution of the product of Example 64B (528 mg, 1.55 mmol) in tetrahydrofuran (40 mL). The resulting gray suspension was heated at reflux under nitrogen for 1 hour and then cooled in ice. The reaction was quenched by successive addition of ethyl acetate (5 mL), water (0.35 ml), 15% NaOH (0.35 mL) and water (1.05 mL). The resulting slurry was stirred for 10 minutes, filtered (tetrahydrofuran (15 mL) and ethyl acetate (15 mL) rinse), and the filtrate was concentrated to provide the title compound, sufficiently pure for use in the next step: 1H NMR (300 MHz, CDCl3) δ ppm 1.78-1.90 (m, 1H), 1.92-2.03 (m, 1H), 2.19-2.31 (m, 1H), 2.44-2.62 (m, J=8.7 Hz, 2H), 2.72-2.85 (m, J=10.7 Hz, 1H), 3.26 (ddd, J=12.1, 5.6, 3.8 Hz, 1H), 3.38-3.62 (m, 6H), 6.67 (dd, J=7.5, 4.5 Hz, 1H), 6.74 (dd, J=7.5, 2.0 Hz, 1H), 6.94-7.06 (m, 2H), 7.28-7.39 (m, 2H), 7.78 (dd, J=4.8, 1.6 Hz, 1H); MS (ESI) m/z 313 (M+H)+.

Provenance & Evidence