Nitrogen → (R)-2-(1-Benzyl-cyclopropylmethyl)-succinic acid 1-methyl ester
Reaktionsgleichung
[CH3:1][O:2][C:3](=[O:20])/[C:4](=[CH:9]\[C:10]1([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:12][CH2:11]1)/[CH2:5][C:6]([OH:8])=[O:7].C[O-].[Na+].N#N>CO>[CH3:1][O:2][C:3](=[O:20])[C@H:4]([CH2:9][C:10]1([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][CH2:12]1)[CH2:5][C:6]([OH:8])=[O:7]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of 2-[1-(1-Benzyl-cyclopropyl)-meth-(Z)-ylidene]-succinic acid 1-methyl ester (2.686 g, 9.79 mmol) and sodium methoxide (0.1 eq., 0.98 mmol, 52.9 mg) in dry methanol (25 mL) was degassed with N2 for 5 min then (+)-(2S,5S)-2,5-Diethylphospholanobenzene (cyclooctadiene) Rhodium tetrafluoroborate (25 mg) was added. The mixture was hydrogenated at 60 psi for 24 hr, then concentrated in vacuum. The residue was diluted with NaHCO3 (150 mL) and the solution was made basic with NaOH and extracted with ether (80 mL). The aqueous layer was acidified to pH 1 and extracted with ether (2×100 mL). The acidic extracts were dried (MgSO4) and concentrated in vacuum to afford (R)-2-(1-Benzyl-cyclopropylmethyl)-succinic acid 1-methyl ester as a yellow oil (2.465 g, 91% yield).
Aufarbeitung
- concentrationconcentrated in vacuum
- additionThe residue was diluted with NaHCO3 (150 mL)
- extractionextracted with ether (80 mL)
- extractionextracted with ether (2×100 mL)
- dry with materialThe acidic extracts were dried (MgSO4)
- concentrationconcentrated in vacuum
Quellen und Nachweise
- ORD-Eintrag
- ord-846f0c91b56c441c8225092d441a1b48
- Quelldatensatz
- uspto-grants-2006_04
- Patentnummer
- US07030116B2
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