Ethyl Acetate → HCID 67980521, Verbindung

HRID 1622305Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1622305
Cl.[CH2:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[CH2:5][CH2:4][NH:3]1.[Br:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C.O>[Br:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:3]2[CH2:4][CH2:5][C:6]3[C:11](=[CH:10][CH:9]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:7]=3)[CH2:2]2)=[CH:19][CH:18]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromideHCID 42614607Methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride

Produkt 1

HCID 67980521HCID 67980521, VerbindungAusbeute 104,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride (500.0 mg, 2.00 mmol) in DMF (17.0 mL) was added 4-bromobenzylbromide (604 mg, 2.42 mmol) and K2CO3 (910 mg, 6.59 mmol). The resulting mixture was stirred overnight at rt. EtOAc and water were added, and the phases were separated. The organic phase was dried over Na2SO4, filtered and concentrated. The resulting residue was purified by column chromatography (SiO2, 0-40% EtOAc in hexane) to give methyl 2-(4-bromobenzyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylate (753 mg, 100%). LC-MS: (FA) ES+ 361; 1H NMR (300 MHz, CDCl3) δ 7.86-7.70 (m, 2H), 7.46 (dd, J=8.7, 2.1 Hz, 2H), 7.36-7.21 (m, 2H), 7.04 (d, J=8.0 Hz, 1H), 3.89 (d, J=3.8 Hz, 3H), 3.64 (s, 4H), 2.93 (t, J=5.8 Hz, 2H), 2.83-2.64 (m, 2H).

Aufarbeitung

  1. customthe phases were separated
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue was purified by column chromatography (SiO2, 0-40% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-15956912804947f5a3d512b5a398d003
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778931B2

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