반응 #92712

반응 방정식

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

N-bromosuccinimide

2,2′-azodiisobutyronitrile

→

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

수율 29.0%

용매

carbon tetrachloride

반응 조건

후처리

1. 1
   workup.ADDITIONwas added portionwise
2. 2
   여과The insoluble material was filtered
3. 3
   workup.ADDITIONan aqueous sodium thiosulfate solution and chloroform were added
4. 4
   기타a layer separation operation
5. 5
   건조After drying over anhydrous sodium sulfate
6. 6
   기타the solvent was evaporated under reduced pressure
7. 7
   기타The obtained residue was purified by silica gel column chromatography

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.

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