HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
2,6-Dimethylmorpholine, cis- → (s)-{1-[3-(cis-2,6-Dimethylmorpholin-4-yl)phenyl]ethyl}-carbamic acid tert-butyl ester
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | 2,6-Dimethylmorpholine, cis- | HCID 641500 | — |
| Edukt | 2-(Di-tert-butylphosphino)biphenyl | HCID 2734215 | — |
| Edukt | Sodium t-butoxide | HCID 23676156 | — |
| Edukt | (S)-N-Boc-1-(3-bromophenyl)ethylamine | HCID 56971804 | — |
| Katalysator | palladium(II) acetate | HCID 167845 | — |
| Lösungsmittel | Toluene | HCID 1140 | — |
| Produkt | (s)-{1-[3-(cis-2,6-Dimethylmorpholin-4-yl)phenyl]ethyl}-carbamic acid tert-butyl ester | HCID 69866002 | 38% |
Reaktionsschritte
A solution of (S)-[1-(3-bromophenyl)ethyl]carbamic acid tert-butyl ester (5 g, 16.7 mmol), cis-2,6-dimethylmorpholine (5.75 g, 3eq.), palladium acetate (5 mol %, 187 mg), 2-(di-t-butylphosphino) biphenyl (10 mol %, 498 mg), and sodium tert-butoxide (1.68 g, 1.05eq) in toluene (33 ml) was stirred at 80° C. for 1.5 hours. The solution was filtered through Celite Pad and washed with ethyl acetate. The filtrate was concentrated under vacuum and purified by flash chromatography with gradient of 20% ethyl acetate/hexane to 30% ethyl acetate/hexane over 20 minutes. The product was obtained as a yellow solid (2.12 g, 38% yield).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US06831080B2 |
| Quelldatensatz | uspto-grants-2004_12 |
| ORD ID | ord-923968d37417419fa28ce7ba51443ad7 |
| Quellennotiz | uspto-grants-2004_12 |