Triethylamine → HCID 86610077, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of phenylmethyl (2R)-5-(2,5-dimethyl-1H-pyrrol-1-yl)-2,3-dihydro-2-methyl-1H-indole-1-carboxylate (Step 3, 2.11 g, 5.84 mmol) in water/ethanol (1:9, 60 mL) is added triethylamine (6.5 mL, 46.7 mmol) and hydroxylamine hydrochloride (6.49 g, 93.4 mmol). The reaction mixture is stirred at 90° C. for 20 h and is then concentrated under reduced pressure. The residue is taken up in CH2Cl2 (60 mL) and washed with H2O (2×20 mL) and saline (2×20 mL), and the combined aqueous layer is extracted with CH2Cl2 (2×20 mL). The combined organic layer is dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the residue is purified by chromatography on a Biotage Flash 40M 90 g silica gel cartridge (30-50% EtOAc/Hexanes eluent) to give the title compound, MS (ESI+) for C17H18N2O2 m/z 283 (M+H)+.

Provenance & Evidence