Aluminium lithium hydride → 2-(4-Benzyloxy-5-fluoro-1H-indol-3-yl)-N,N-dimethylethanamine

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Reaction Steps

A solution of 1-6a (2.26 g, 6.647 mmol) in dry 1,4-dioxane (30 mL) was added dropwise to a slurry of LiAlH4 (2.52 g, 66.47 mmol) in dry 1,4-dioxane (40 mL) at reflux. The mixture was held at reflux for 1 h. The mixture was then cooled, quenched with ice-water (mixed with NaOH), filtered through Celite, and the filter cake was washed with EtOAc. The filtrate and EtOAc washings were combined and extracted three times with EtOAc. The organic layer was washed with 1 N NaOH and brine, dried over Na2SO4 and concentrated. The resulting residue was purified by column chromatography on silica gel with CH2Cl2 (100%) to 5% NH4OH in CH2Cl2 as eluent to give the product (1-7a) as a brown oil in 80% yield, 1.67 g. 1H NMR (300 MHz, CDCl3-d) δ (ppm) 2.14 (s, 6H). 2.52-2.57 (m, 2H), 2.91-2.97 (m, 2H), 5.25 (s, 2H), 6.92-6.98 (m, 3H), 7.31-7.40 (m, 3H), 7.49-7.52 (m, 2H), 7.97 (br, 1H). APCI [M+1]: 313.1.

Provenance & Evidence