Methanol → 1-benzyl-4-tert-butyloxycarbonyl-2,7-dioxo-2,3,4,5,6,7-hexahydro-1H-1,4-benzodiazonine

HRID 1106923Notes

Reaction equation

HRID 1106923 reaction equation
[O:1]=[O+][O-].[CH2:4]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)C2[CH2:20][CH2:21][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:23][C:12]1=2)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CSC.[CH3:34][OH:35]>>[CH2:4]([N:11]1[C:19]2[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=2[C:34](=[O:35])[CH2:20][CH2:21][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:23][C:12]1=[O:1])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 24823OzoneHCID 183772769-benzyl-2-tert-butyloxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole

Product 1

HCID 187882101-benzyl-4-tert-butyloxycarbonyl-2,7-dioxo-2,3,4,5,6,7-hexahydro-1H-1,4-benzodiazonine

Procedure

Ozone was bubbled through a solution of 9-benzyl-2-tert-butyloxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole (6.0 g, 16.6 mmol) in methanol (90 ml) at -78° C. until a blue colour persisted. Nitrogen was then bubbled through the solution until clear, followed by the addition of dimethyl sulphide (12.0 ml, 163 mmol). The solution was allowed to warm to room temperature and stirring continued for a further 2 hours, followed by evaporation to dryness. The crude product was purified by chromatography on silica gel with ethyl acetate-hexane (1:1) as eluant. (6.0 g, 92%).

Workup

  1. customNitrogen was then bubbled through the solution until clear,
  2. customfollowed by evaporation to dryness
  3. customThe crude product was purified by chromatography on silica gel with ethyl acetate-hexane (1:1) as eluant

Sources & evidence

ORD record
ord-fd39eb218a3e4c4db035490fd4636796
Source dataset
uspto-grants-2000_05
Patent number
US06057311

Reaction notes

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