Benzyl chloroformate → Benzyl 7-nitro-1,2,3,4-tetrahydroisoquinoline-2-carboxylate
Reaktionsgleichung
Cl.[N+:2]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][NH:11][CH2:12]2)=[CH:7][CH:6]=1)([O-:4])=[O:3].C([O-])([O-])=O.[K+].[K+].Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>CCOC(C)=O.O>[CH2:25]([O:24][C:22]([N:11]1[CH2:10][CH2:9][C:8]2[C:13](=[CH:14][C:5]([N+:2]([O-:4])=[O:3])=[CH:6][CH:7]=2)[CH2:12]1)=[O:23])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a solution of 7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride (11.0 g, 51.25 mmol) in EtOAc (150 mL) at 0° C. in an ice bath add a solution of K2CO3 (15.65 g, 113.25 mmol) in water (150 mL) followed by benzyl chloroformate (8.37 mL, 56.37 mmol) and vigorously stir the reaction at room temperature for 24 h. Separate the layers and extract the aqeuous with more EtOAc (150 mL). Wash the organics with sat. NaHCO3 (200 mL), sat. NH4Cl (200 mL) and water (200 mL), then dry (Na2SO4). Concentrate in vacuo to give 14.70 g of 7-nitro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester as an oil which partially crystallizes.
Aufarbeitung
- customthe reaction at room temperature for 24 h
- customSeparate the layers
- extractionextract the aqeuous with more EtOAc (150 mL)
- washWash the organics with sat. NaHCO3 (200 mL), sat. NH4Cl (200 mL) and water (200 mL)
- dry with materialdry (Na2SO4)
- concentrationConcentrate in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-3ae326eec657426ebaa0390190a2c4ad
- Quelldatensatz
- uspto-grants-2015_07
- Patentnummer
- US09079880B2
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