Chlorotrimethylsilane → (3R*,4R*)-N,N-Diethyl-6-diphenylmethyl-5,5-ethylenedioxy-1-azabicyclo[2.2.2]octane-3-carboxamide

HRID 862117노트

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HRID 862117 반응식
[CH2:1]([N:3]([CH2:28][CH3:29])[C:4]([C@@H:6]1[C@H: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]([C@@H:6]1[C@H: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 53867571(3R*,4R*)-N,N-diethyl-6-diphenylmethyl-5-oxo-1-azabicyclo[2.2.2]octane-3-carboxamide

생성물 1

HCID 53633469(3R*,4R*)-N,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)
  2. additionthe mixture was 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-b85c32bb7899450d9dc721ec2939af69
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05716965

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