Methanol → 7,7-Dimethyl-2-methylamino-5-pentyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one

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Reaction Steps

Freshly cut sodium (300 mg) is dissolved in dry MeOH (12 ml) and D5 (700 mg) is added and the mixture stirred for 5 min. Then p-formaldehyde (102 mg; 3.4 mmol) is added and the mixture stirred for 20 h at RT. After the addition of NaBH4 (93 mg; 2.46 mmol) the solution is heated under reflux for 2 h, cooled to RT and diluted with water. The aqueous layer is extracted with EtOAc. The combined organic layer is washed with brine, dried over Na2SO4 and concentrated in vacuo. The compound (700 mg) is obtained by flash chromatography on silica gel eluted with CH2Cl2/MeOH (95:5).

Provenance & Evidence