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

HRID 64434노트

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HRID 64434 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fb5760943c3e424483425be10e2c90d6
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447090B2

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