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

HRID 1458893Notes

Reaction equation

HRID 1458893 reaction equation
[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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
100 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-6a46400dfc3845c4baf93917236efac7
Source dataset
uspto-grants-1998_12
Patent number
US05852038

Reaction notes

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