Azobisisobutyronitrile → tert-butyl[(1R,2S)-3-bromo-2-(methoxymethoxy)-2,3-dihydro-1H-inden-1-yl](methoxymethyl)carbamate

HRID 64434ノート

反応式

HRID 64434 の反応式
[C:1]([O:5][C:6](=[O:24])[N:7]([C@@H:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][C@H:12]1[O:20][CH2:21][O:22][CH3:23])[CH2:8][O:9][CH3:10])([CH3:4])([CH3:3])[CH3:2].[Br:25]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:24])[N:7]([C@@H:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]([Br:25])[C@H:12]1[O:20][CH2:21][O:22][CH3:23])[CH2:8][O:9][CH3:10])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 86713447tert-butyl [(1R,2R)-2-(methoxymethoxy)-2,3-dihydro-1H-inden-1-yl](methoxymethyl)carbamate

生成物 1

HCID 86713449tert-butyl[(1R,2S)-3-bromo-2-(methoxymethoxy)-2,3-dihydro-1H-inden-1-yl](methoxymethyl)carbamate収率 29%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

反応条件

温度
100 °C

実験手順

A solution of 2.75 g of tert-butyl[(1R,2R)-2-(methoxymethoxy)-2,3-dihydro-1H-inden-1-yl](methoxymethyl)carbamate in 55 ml of carbon tetrachloride was heated at an outer temperature of 100° C., and a mixture of 1.53 g of N-bromosuccinimide and 95 mg of 2,2′-azodiisobutyronitrile was added portionwise thereto over 30 minutes at an interval of 5 minutes, followed by stirring at an outer temperature of 100° C. for 1 hour. The insoluble material was filtered, and an aqueous sodium thiosulfate solution and chloroform were added thereto to carry out a layer separation operation. After drying over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 984 mg of tert-butyl[(1R,2S)-3-bromo-2-(methoxymethoxy)-2,3-dihydro-1H-inden-1-yl](methoxymethyl)carbamate.

後処理

  1. additionwas added portionwise
  2. filtrationThe insoluble material was filtered
  3. additionan aqueous sodium thiosulfate solution and chloroform were added
  4. customa layer separation operation
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-fb5760943c3e424483425be10e2c90d6
出典データセット
uspto-grants-2016_09
特許番号
US09447090B2

反応ノート

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