HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Trifluoroacetic acid → 1'-(Bicyclo[2.2.1]hept-5-en-2-ylmethyl)spiro[isoindoline-1,4'-piperidin]-3-one
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Trifluoroacetic acid | HCID 6422 | — |
| Edukt | Bicyclo(2.2.1)hept-5-ene-2-carboxaldehyde | HCID 95117 | — |
| Edukt | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Edukt | Spiro[isoindoline-1,4'-piperidin]-3-one | HCID 15548169 | — |
| Lösungsmittel | 1,2-Dichloroethane | HCID 11 | — |
| Lösungsmittel | Acetonitrile--water (1/1) | HCID 18373917 | — |
| Produkt | 1'-(Bicyclo[2.2.1]hept-5-en-2-ylmethyl)spiro[isoindoline-1,4'-piperidin]-3-one | HCID 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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US07863449B2 |
| Quelldatensatz | uspto-grants-2011_01 |
| ORD ID | ord-8aef3106e8204065a3a9a129e087fa9a |
| Quellennotiz | uspto-grants-2011_01 |