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

HRID 1458893ノート

反応式

HRID 1458893 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 174Ethylene Glycol溶媒

反応条件

温度
100 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-6a46400dfc3845c4baf93917236efac7
出典データセット
uspto-grants-1998_12
特許番号
US05852038

反応ノート

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