Methyl Isocyanate → 5-(methylaminocarbonyl-N-methylamino)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indole

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Reaction Steps

5-(t-Butoxycarbonyl-N-methylamino)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indole (100 mg) was heated under nitrogen without solvent to 200°-210° C. in an oil bath. After 1 hour, TLC (thin layer chromatography) indicated a conversion to a new compound. The flask was allowed to cool to ambient temperature and dichloromethane (5 ml) was added followed by the slow addition of a solution of methyl isocyanate (18 mg) in dichloromethane (3 ml) over a period of 45 minutes. The mixture was washed with water (2 ml), dried (Na2SO4), concentrated and purified by flash chromatography (eluting with 15% MeOH/EtOAc). The pure fractions were concentrated to give 5-(methylaminocarbonyl-N-methylamino)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indole (0.05 g).

Provenance & Evidence