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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 341487Erstellt: 25. Oktober 2026

1,2-Dimethoxyethane → tert-Butyl 3-cyano-8-azabicyclo[3.2.1]octane-8-carboxylate

https://huagongshe.com/reaction/341487

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
Edukt1,2-DimethoxyethaneHCID 8071—
EduktTosylmethyl isocyanideHCID 161915—
Edukttert-Butyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylateHCID 2794767—
EduktPotassium tert-butoxideHCID 23665647—
LösungsmittelEthanolHCID 702—
Produkttert-Butyl 3-cyano-8-azabicyclo[3.2.1]octane-8-carboxylateHCID 5348765869%

Reaktionsschritte

To 3-oxo-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (300 mg, 1.33 mmol) was added DME (9 mL) and EtOH (0.2 mL). The mixture was cooled to 0 C when TOSMIC (530 mg, 2.65 mmol) and potassium tert-butoxide (609 mg, 5.2 mmol) were added. The mixture was stirred to room temperature and then heated at 50 C for 18 h. After this time the reaction was evaporated and loaded onto a silica column and eluted with heptane-10% to 30% ethyl actetate to give the title compound (216 mg, 69%). Method B HPLC-MS: MH+ requires m/z=237. Found: m/z=237, Rt=1.35 min (86%).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08895733B2
Quelldatensatzuspto-grants-2014_11
ORD IDord-cc049e06862c452cb77dc68bb0597096
Quellennotizuspto-grants-2014_11