Reaktion #949299

Reaktionsgleichung

(3R*,4R*)-N,N-diethyl-6-diphenylmethyl-5-oxo-1-azabicyclo[2.2.2]octane-3-carboxamide

1,2-bis(trimethylsiloxy)ethane

trimethylsilyl chloride

→

21

Ausbeute 88.5%

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

Ausbeute 88.5%

Lösungsmittel

ethylene glycol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter by-products were removed by distillation (93° C./atmosphere pressure)
2. 2
   workup.ADDITIONthe mixture was poured into cold aqueous sodium bicarbonate (NaHCO3) (250 ml)
3. 3
   Extraktionextracted with methylene chloride (CH2Cl2) (100 ml) three times
4. 4
   TrocknenThe combined extracts were dried over sodium sulfate (Na2SO4)
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe clude was purified by recrystallization from ethyl acetate (EtOAc)/hexane

Vorschrift

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%).

Quelle