Acetic Acid → HCID 21955940, compound

Participants

Reaction Steps

A solution of 3-(2-oxo-cyclopentylmethyl)-1H-indole-5-carbonitrile (45 mg, 0.19 mMol), dimethylamine (1.92 mL, 3.78 mMol, 2.0 M/THF), sodium cyanoborohydride (0.12 g, 1.9 mMol) and acetic acid (0.2 mL) in ethanol (10 mL) was stirred for 16 h. The solution was cooled in an ice-bath and quenched with aqueous hydrochloric acid (2 mL, 1 N). The mixture was stirred for 5 min and then poured into a saturated aqueous solution of sodium bicarbonate (15 mL) and brine (10 mL). The aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with brine (20 mL), dried over anhydrous sodium sulfate, and concentrated in vacuo. The crude material was purified by silica gel column chromatography using a step gradient of 0.5% MeOH/CHCl3-30% MeOH/CHCl3 to give 3-(2-dimethylamino-cyclopentylmethyl)-1H-indole-5-carbonitrile (13.0 mg, 26%) as a mixture of diastereomers. 1H NMR (400 MHz, DMSO-d6) δ 7.98 (1H, s), 7.50 (1H, d, J=8.4 Hz), 7.38 (2H, m), 2.89 (1H, m), 2.33 (9H, m), 1.82 (2H, m), 1.57 (2H, m), 1.42 (2H, m); LCMS (Method A: 4.6×50 mm XTERRA C-18 S5 column, 5 mL/min, 0–100% MeOH/H2O/0.1% TFA, 2 min gradient): Tr=1.09 min, m/e 268 (M+H)+.

Provenance & Evidence