Water → 1-{(3aS,7E,7aR)-7-(bromomethylene)-3a,4,5,6,7,7a-hexahydro-3a-methyl-1H-indene-3-yl}ethanone

HRID 1922626노트

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HRID 1922626 반응식
Br[C@@:2]1([C:14](=[O:16])[CH3:15])[C@:10]2([CH3:11])[C@H:5](/[C:6](=[CH:12]/[Br:13])/[CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3]1.[Br-].[Li+].C(=O)([O-])[O-].[Li+].[Li+].O>CN(C)C=O>[Br:13]/[CH:12]=[C:6]1\[CH2:7][CH2:8][CH2:9][C@@:10]2([CH3:11])[C@H:5]\1[CH2:4][CH:3]=[C:2]2[C:14](=[O:16])[CH3:15]

참가 물질

6

반응물 4

HCID 962WaterHCID 11125Lithium CarbonateHCID 82050Lithium BromideHCID 594565421-{(E,1R,3aS,7aS)-1-bromo-4-(bromomethylene)-octahydro-7a-methyl-1H-indene-1-yl}ethanone2회

생성물 1

HCID 594565491-{(3aS,7E,7aR)-7-(bromomethylene)-3a,4,5,6,7,7a-hexahydro-3a-methyl-1H-indene-3-yl}ethanone수율 94%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

1-{(E,1R,3aS,7aS)-1-bromo-4-(bromomethylene)-octahydro-7a-methyl-1H-indene-1-yl}ethanone (Compound 12: 100 mg, 0.369 mmol) was dissolved in dimethylformamide (1.6 ml), and lithium bromide (35.8 mg, 0.412 mmol) and lithium carbonate (27.4 mg, 0.371 mmol) were added thereto. The resulting mixture was heated to 100° C. and stirred for 3 hours. After cooling the reaction solution to room temperature, water was added thereto, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with saturated brine, dried over sodium sulfate, and evaporated to obtain a crude product. The product was purified by flash column chromatography to obtain 1-{(3aS,7E,7aR)-7-(bromomethylene)-3a,4,5,6,7,7a-hexahydro-3a-methyl-1H-indene-3-yl}ethanone (71.6 mg, 94.0%) as a white solid.

후처리

  1. temperatureAfter cooling the reaction solution to room temperature
  2. extractionthe resulting mixture was extracted with diethyl ether
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customto obtain a crude product
  7. customThe product was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-c008845b63ed4517b566228e26c40fb7
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173824B2

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