Aluminium lithium hydride → HCID 59732469, compound

Participants

Reaction Steps

To a solution of [2-[(4-ethoxyphenyl)methyl]-1-[(tetrahydro-2H-pyran-4-yl)methyl]-1H-pyrrolo[2,3-b]pyridin-5-yl]-carbamic acid methyl ester (153 mg, 0.36 mmol) in THF (25 ml) at 0° C. was added lithium aluminum hydride (35 mg, 0.90 mmol). The mixture was stirred for 48 hours at room temperature. The reaction was then cooled to 0° C. and quenched by dropwise addition of water (35 □L), followed by 4M NaOH aqueous solution (35 μL) and water (105 μL). After stirring at room temperature for 30 minutes, the suspension was filtered over Diatomaceous earth and concentrated in vacuo to give 100 mgs of colorless oil. 1H NMR (400 MHz, CHLOROFORM-D) δ 1.40 (m, 5 H), 1.59 (m, 2 H), 2.05 (m, 1 H), 2.87 (s, 3 H), 3.36 (m, 2 H), 3.66 (m, 2 H), 4.01 (m, 6 H), 5.99 (s, 1 H), 6.83 (d, J=8.79 Hz, 2 H), 6.98 (s, 1 H), 7.05 (d, J=2.54 Hz, 1 H), 7.10 (d, J=8.79 Hz, 2 H), 7.79 (d, J=2.54 Hz, 1 H). MS (ESI) (M+H)+: 380.

Provenance & Evidence