Ammonium Chloride → 4-(Benzyloxycarbonylamino)cyclohexylidenemethyl methyl ether

HRID 1682649노트

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HRID 1682649 반응식
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.[CH2:29]([O:36][C:37]([NH:39][CH:40]1[CH2:45][CH2:44][C:43](=O)[CH2:42][CH2:41]1)=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[Cl-].[NH4+]>CCCCCC.O1CCCC1>[CH3:2][O:3][CH:4]=[C:43]1[CH2:44][CH2:45][CH:40]([NH:39][C:37]([O:36][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:38])[CH2:41][CH2:42]1

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 14615292Benzyl (4-oxocyclohexyl)carbamateHCID 178418339Butyllithium

생성물 1

HCID 189194024-(Benzyloxycarbonylamino)cyclohexylidenemethyl methyl ether수율 32%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

Tetrahydrofuran (280 ml) was added to (methoxymethyl)triphenylphosphonium chloride (27.8 g, 81.1 mmol) and a solution (50.0 ml, 80.0 mmol) of 1.6M n-butyllithium in n-hexane was dropwise added at -40° C. over 30 minutes, which was followed by stirring for one hour. Then, a solution of 4-(benzyloxycarbonylamino) cyclohexanone (20.0 g, 81.0 mmol) dissolved in tetrahydrofuran (200 ml) was dropwise added over 30 minutes. The mixture was warmed to room temperature and stirred for 3.5 hours. The reaction mixture was poured into a saturated aqueous ammonium chloride solution and the organic layer was separated. The aqueous layer was extracted with ethyl acetate and the extract and the organic layer were combined. The mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. After filtration, low boiling matters were distilled away from the filtrate under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to give 7.02 g of 4-(benzyloxycarbonylamino)cyclohexylidenemethyl methyl ether as a colorless solid (32%).

후처리

  1. additionwas dropwise added over 30 minutes
  2. stirringstirred for 3.5 hours
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. extractionthe extract
  6. washThe mixture was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter filtration, low boiling matters
  9. distillationwere distilled away from the filtrate under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1)

출처 및 근거

ORD 기록
ord-6b796db62aff426a8ed5050dbd2a6f60
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05635527

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