Chlorotrimethylsilane → N,N-Diethyl-6-diphenylmethyl-5,5-ethylenedioxy-1-azabicyclo-[2.2.2]octane-3-carboxamide

HRID 1458893

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HRID 1458893 반응식
[CH2:1]([N:3]([CH2:28][CH3:29])[C:4]([CH:6]1[CH:11]2[CH2:12][CH2:13][N:8]([CH:9]([CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10]2=[O:14])[CH2:7]1)=[O:5])[CH3:2].C[Si](C)(C)[O:32][CH2:33][CH2:34]O[Si](C)(C)C.C[Si](Cl)(C)C>C(O)CO>[CH2:28]([N:3]([CH2:1][CH3:2])[C:4]([CH:6]1[CH:11]2[CH2:12][CH2:13][N:8]([CH:9]([CH:15]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:10]32[O:32][CH2:33][CH2:34][O:14]3)[CH2:7]1)=[O:5])[CH3:29]

참가 물질

5

반응물 3

HCID 6397ChlorotrimethylsilaneHCID 818582,2,7,7-Tetramethyl-3,6-dioxa-2,7-disilaoctaneHCID 21862301N,N-diethyl-6-diphenylmethyl-5-oxo-1-azabicyclo[2.2.2]octane-3-carboxamide

생성물 1

HCID 53633468N,N-Diethyl-6-diphenylmethyl-5,5-ethylenedioxy-1-azabicyclo-[2.2.2]octane-3-carboxamide수율 88.5%

시약·촉매·용매 1

HCID 174Ethylene Glycol용매

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온도
100 °C

실험 절차

A mixture of (3R*, 4R*)-N,N-diethyl-6-diphenylmethyl-5-oxo-1-azabicyclo[2.2.2]octane-3-carboxamide (10 g, 26 mmol), 1,2-bis(trimethylsiloxy)ethane (6 g, 29 mmol), trimethylsilyl chloride (20 ml) and ethylene glycol (50 ml) was heated at 100° C. for 3 hours. After by-products were removed by distillation 93° C./atmosphere pressure), the mixture was poured into cold aqueous sodium bicarbonate (NaHCO3) (250 ml) and extracted with methylene chloride (CH2Cl2) (100 ml) three times. The combined extracts were dried over sodium sulfate (Na2SO4) and concentrated. The clude was purified by recrystallization from ethyl acetate (EtOAc)/hexane to give 21 (1:2 mixture at 6-position; 23 mmol, 88%).

후처리

  1. customAfter by-products were removed by distillation 93° C./atmosphere pressure), the mixture
  2. additionwas poured into cold aqueous sodium bicarbonate (NaHCO3) (250 ml)
  3. extractionextracted with methylene chloride (CH2Cl2) (100 ml) three times
  4. dry with materialThe combined extracts were dried over sodium sulfate (Na2SO4)
  5. concentrationconcentrated
  6. customThe clude was purified by recrystallization from ethyl acetate (EtOAc)/hexane

출처 및 근거

ORD 기록
ord-6a46400dfc3845c4baf93917236efac7
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05852038

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