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

HRID 703541Notes

Reaction equation

HRID 703541 reaction equation
C([O:5][C:6]([N:8]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH3:19])[CH:14]1[N:20]([CH3:23])[CH2:21][CH2:22][C:13]21[CH3:24])[CH3:9])=O)(C)(C)C.[CH3:25][N:26]=C=O>ClCCl>[CH3:25][NH:26][C:6]([N:8]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH3:19])[CH:14]1[N:20]([CH3:23])[CH2:21][CH2:22][C:13]21[CH3:24])[CH3:9])=[O:5]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 199089055-(t-butoxycarbonyl-N-methylamino)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indole

Product 1

HCID 199089295-(methylaminocarbonyl-N-methylamino)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indoleYield 57.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  1. washThe mixture was washed with water (2 ml)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified by flash chromatography (eluting with 15% MeOH/EtOAc)
  5. concentrationThe pure fractions were concentrated

Sources & evidence

ORD record
ord-c488b30a71cf422ba35b3a7319b8de8b
Source dataset
uspto-grants-1991_01
Patent number
US04983616

Reaction notes

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