Chlorotrimethylsilane → HCID 53633468, Verbindung

HRID 1458893

Reaktionsgleichung

[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]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

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%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-6a46400dfc3845c4baf93917236efac7
Quelldatensatz: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05852038

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