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

HRID 1106923ノート

反応式

HRID 1106923 の反応式
[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

参加物

5

反応物 4

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

生成物 1

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

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-fd39eb218a3e4c4db035490fd4636796
出典データセット
uspto-grants-2000_05
特許番号
US06057311

反応ノート

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