Zurück
HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 251475Erstellt: 26. Oktober 2026

Trifluoroacetic acid → 1'-(Bicyclo[2.2.1]hept-5-en-2-ylmethyl)spiro[isoindoline-1,4'-piperidin]-3-one

https://huagongshe.com/reaction/251475

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktTrifluoroacetic acidHCID 6422—
EduktBicyclo(2.2.1)hept-5-ene-2-carboxaldehydeHCID 95117—
EduktSodium triacetoxyborohydrideHCID 5049666—
EduktSpiro[isoindoline-1,4'-piperidin]-3-oneHCID 15548169—
Lösungsmittel1,2-DichloroethaneHCID 11—
LösungsmittelAcetonitrile--water (1/1)HCID 18373917—
Produkt1'-(Bicyclo[2.2.1]hept-5-en-2-ylmethyl)spiro[isoindoline-1,4'-piperidin]-3-oneHCID 58089627—

Reaktionsschritte

Sodium triacetoxyborohydride (31 mg, 0.15 mmol) was added to a stirred solution of spiro[isoindoline-1,4′-piperidin]-3-one 3a (20 mg, 0.10 mmol) and bicyclo[2.2.1]hept-5-ene-2-carbaldehyde (18 mg, 0.15 mmol) in 1,2-dichloroethane (1 mL) and the mixture was stirred at room temperature for 6 h. The solvent was removed under reduced pressure and the crude product was purified by preparative HPLC (5-70% CH3CN—H2O gradient with 0.05% TFA, 15 min) to give compound no. 267. LC/MS m/z [M+H]+ 309.0 retention time 1.7 min (10-90% CH3CN—H2O gradient, with 0.05% TFA, 5 min).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS07863449B2
Quelldatensatzuspto-grants-2011_01
ORD IDord-8aef3106e8204065a3a9a129e087fa9a
Quellennotizuspto-grants-2011_01