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

HRID 862117ノート

反応式

HRID 862117 の反応式
[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]

参加物

5

反応物 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

生成物 1

HCID 53633469(3R*,4R*)-N,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)
  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

出典と根拠

ORDレコード
ord-b85c32bb7899450d9dc721ec2939af69
出典データセット
uspto-grants-1998_02
特許番号
US05716965

反応ノート

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