Aluminium lithium hydride → HCID 22638687, compound

Participants

Reaction Steps

A solution of (−)-trans-2-(5-fluoro-3-indolylcarbonyl)-cyclopropanecarboxylic acid dimethylamide (180 mg, 0.66 mmol) in THF was added dropwise to a suspension of LAH (100 mg, 2.63 mmol) in THF at room temperature with stirring. The reaction was heated to reflux and stirred for 1 h. The reaction was then cooled to room temperature, diluted with ether, and quenched with aqueous NaOH (1 mL of 1 N solution). The resulting precipitate was filtered and washed with ether. The organic filtrate was concentrated in vacuo. The residue was dissolved in methylene chloride, and transferred directly to an SCX resin cartridge. The cartridge was washed with methanol, and then with methanolic ammonia (2.0 M) to give (+)-[2-(5-fluoro-1H-indol-3-ylmethyl)-cyclopropyl-methyl]-dimethylamine [150 mg, 94% yield, optical rotation +19.26° (c=1.38 mg/mL, ethanol, 20° C.)]. 1H NMR (MeOH-d4): δ7.25 (dd, J=8.8, 4.5 Hz, 1H), 7.17 (dd, J=9.9, 2.5 Hz, 1H), 6.82 (dt, J=2.4 Hz, 1H), 2.69 (dd, J=6.5 Hz, 2H), 2.29 (dd, J=4.86 Hz, 1H), 2.20 (s, 6H), 2.15 (dd, J=12.8 Hz, 1H), 0.90 (m, 1H), 0.70 (m, 1H), 0.51 (m, 1H), and 0.39 (m, 1H), FIMS: 247.3 (M+H)+.

Provenance & Evidence