HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Methanol → (R,R)-N-[4-(3-trifluoromethylphenyl)-2-butyl]-1-(1-naphthyl)ethylamine
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Methanol | HCID 887 | — |
| Edukt | (+)-1-(1-Naphthyl)ethylamine | HCID 2724264 | — |
| Edukt | Sodium cyanoborohydride | HCID 5003444 | — |
| Edukt | 4-[3-(Trifluoromethyl)phenyl]butan-2-one | HCID 13339059 | — |
| Katalysator | Titanium isopropoxide | HCID 11026 | — |
| Lösungsmittel | Chloroform | HCID 6212 | — |
| Produkt | (R,R)-N-[4-(3-trifluoromethylphenyl)-2-butyl]-1-(1-naphthyl)ethylamine | HCID 9951316 | — |
| Produkt | (S,R)-N-[4-(3-trifluoromethylphenyl)-2-butyl]-1-(1-naphthyl)ethylamine | HCID 53733257 | — |
Reaktionsschritte
In a similar fashion an equal molar amount of 4-(3-trifluoromethylphenyl)-2-butanone, (R)-1-(1-naphthyl)ethylamine and 1.25 equivalents titanium(IV) isopropoxide were mixed and the intermediate imine reduced with ethanolic sodium cyanoborohydride. Work-up and repetitive preparative thin-layer chromatography using 5% methanol in chloroform afforded (S,R)-N-[4-(3-trifluoromethylphenyl)-2-butyl]-1-(1-naphthyl)ethylamine, 25C [m/z (rel. int.) 371 (M+, 3), 356 (16), 198 (15), 155 (100), 129 (8),115 (5),109 (3), 77 (2)] and (R,R)-N-[4-(3-trifluoromethylphenyl)-2-butyl]-1-(1-naphthyl)ethylamine, 25D; m/z (rel. int.) 371 (M+, 3), 356 (16), 198 (15), 155 (100), 129 (8), 115 (5), 109 (3), 77 (2).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US06211244B1 |
| Quelldatensatz | uspto-grants-2001_04 |
| ORD ID | ord-b89a225fdf774d84bf1806a839a76f6f |
| Quellennotiz | uspto-grants-2001_04 |