Reaktionsgleichung
C(OC(=O)[NH:7][CH2:8][CH2:9][C:10]#[C:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(C)(C)C>N1C=CC=CC=1.[Pd]>[C:12]1(/[CH:11]=[CH:10]\[CH2:9][CH2:8][NH2:7])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1Komponenten
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A suspension of palladium on barium sulfate (15 mg) was stirred for 15 min in 1 mL pyridine. (4-phenyl-but-3-ynyl)-carbamic acid tert-butyl ester (66 mg) was added and the solution was purged with hydrogen then stirred for 1 h under a hydrogen-filled balloon. The solution was diluted with ethyl acetate (10 ml) and washed 3 times with 1 N hydrochloric acid (10 ml). The ethyl acetate layer was dried over sodium sulfate and filtered. The filtrate was evaporated and the resulting residue (54 mg) is primarily cis-(4-phenyl-but-3-enyl)-carbamic acid tert-butyl ester along with (4-phenyl-but-3-ynyl)-carbamic acid tert-butyl ester, 4-phenylbutylamine, and trans-(4-phenyl-but-3-enyl)-carbamic acid tert-butyl ester. The combined minor products constitute ˜20% of the crude material. The tert-butoxycarbonyl group of the desired product was removed by Procedure P to give cis-4-phenyl-but-3-enylamine, which was used in subsequent transformations without further purification.
Aufarbeitung
- customthe solution was purged with hydrogen
- additionfilled balloon
- additionThe solution was diluted with ethyl acetate (10 ml)
- washwashed 3 times with 1 N hydrochloric acid (10 ml)
- dry with materialThe ethyl acetate layer was dried over sodium sulfate
- filtrationfiltered
- customThe filtrate was evaporated
- customThe tert-butoxycarbonyl group of the desired product was removed by Procedure P
Quellen und Nachweise
- ORD-Eintrag
- ord-1ba07cbda9804effb51403d0992a3d41
- Quelldatensatz
- uspto-grants-2006_08
- Patentnummer
- US07084154B2
Verknüpfte Notizen
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