Aluminium lithium hydride → HCID 67001448, compound

Participants

Reaction Steps

Solid LiAlH4 (100 mg, 2.63 mmol) was added to a stirred solution of the product of Example 22E (72 mg, 0.311 mmol) in tetrahydrofuran (10 mL) at room temperature. The resulting mixture was heated at reflux under nitrogen for 2 hours, then cooled in ice and quenched by successive addition of ethyl acetate (4 mL), water (0.1 mL), 15% NaOH (0.1 mL) and water (0.3 mL). The mixture was filtered through a pad of diatomaceous earth with an ethyl acetate (25 mL total) rinse. The filtrate was concentrated under vacuum to provide the title compound, sufficiently pure for use in the next step: 1H NMR (300 MHz, CDCl3) δ ppm 2.06-2.20 (m, 2H), 2.25-2.42 (m, 2H), 2.37 (s, 3H), 2.62 (d, J=9.5 Hz, 1H), 2.77-2.87 (m, 1H), 3.08 (dt, J=11.6, 3.1 Hz, 1H), 3.18 (ddd, J=12.2, 5.3, 2.8 Hz, 1H), 3.22-3.33 (m, 1H), 3.64-3.75 (m, 2H), 6.53 (dd, J=7.5, 2.0 Hz, 1H), 6.76 (td, J=7.4, 1.8 Hz, 1H), 6.83 (td, J=7.4, 1.8 Hz, 1H), 6.92 (dd, J=7.5, 1.6 Hz, 1H); MS (DCI) m/z 218 (M+H)+.

Provenance & Evidence