Reaktionsgleichung
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][C:20]=1[CH2:21]Br)[C:14]([O:16][CH3:17])=[O:15].C(N(CC)CC)C>O1CCCC1>[CH2:1]([N:8]1[CH2:10][C:11]2[C:20](=[CH:19][CH:18]=[C:13]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=2)[CH2:21]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Benzylamine (3.21 g, 30.0 mmol) in anhydrous tetrahydrofuran (25 ml) was added to a stirred mixture of methyl 3,4-bis-(bromomethyl)benzoate (9.66 g, 30.0 mmol) (obtained from Fluorochem) and triethylamine (9 ml, 64.7 mmol) in anhydrous tetrahydrofuran (50 ml) and the resulting mixture was stirred at room temperature for 3 hours. The solvent was removed in vacuo at 40° C. and the residue partitioned between ethyl acetate (100 ml) and water (100 ml). The organic layer was washed with a further portion of water (100 ml), separated and the solvent removed in vacuo at 40° C. to afford methyl 2-benzyl-2,3-dihydro-1H-isoindole-5-carboxylate as a pale orange solid that was used immediately without further purification as described below. 1H NMR (DMSO-d6) 7.82 (2H, m), 7.40-7.25 (6H, m), 3.90 (3H, s), 3.88 (2H, s), 3.84 (4H, s). MS: [M+H]+ 268.
Aufarbeitung
- customThe solvent was removed in vacuo at 40° C.
- customthe residue partitioned between ethyl acetate (100 ml) and water (100 ml)
- washThe organic layer was washed with a further portion of water (100 ml)
- customseparated
- customthe solvent removed in vacuo at 40° C.
Quellen und Nachweise
- ORD-Eintrag
- ord-ed37ff92a00949a9bd5d3c3d49175bde
- Quelldatensatz
- uspto-grants-2014_11
- Patentnummer
- US08883790B2
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