4-Methylmorpholine → Tert-butyl[2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]carbamate

HRID 2383017Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2383017
Cl.[CH:2]1([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][NH:9]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C(Cl)(=O)C(C)(C)C.CN1CCOCC1.[C:32]([O:36][C:37]([NH:39][CH2:40][C:41](O)=[O:42])=[O:38])([CH3:35])([CH3:34])[CH3:33]>C(Cl)Cl.O>[C:32]([O:36][C:37](=[O:38])[NH:39][CH2:40][C:41]([N:9]1[CH2:10][CH2:11][C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]1[CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1)=[O:42])([CH3:35])([CH3:33])[CH3:34]

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 62493Pivaloyl chlorideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 675358401-Cyclohexyl-1,2,3,4-tetrahydroisoquinoline hydrochloride

Produkt 1

HCID 68250253Tert-butyl[2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]carbamateAusbeute 100,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline hydrochloride (1.00 g) was dissolved in methylene chloride (20 mL), and pivaloyl chloride (0.98 mL) and 4-methylmorpholine (2.2 mL) were added thereto under ice-cooling. The reaction liquid was stirred at room temperature for 30 minutes and then ice-cooled, and [(tert-butoxycarbonyl)amino]acetic acid (1.54 g) was added thereto. The reaction liquid was stirred at room temperature for 14 hours and then water was added thereto, followed by extraction with chloroform. The extract was washed with saturated brine, and then dried over magnesium sulfate. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography (chloroform-MeOH) to obtain tert-butyl[2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]carbamate (1.49 g).

Aufarbeitung

  1. temperatureunder ice-cooling
  2. customThe reaction liquid
  3. temperatureice-cooled
  4. customThe reaction liquid
  5. stirringwas stirred at room temperature for 14 hours
  6. extractionfollowed by extraction with chloroform
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was evaporated
  10. customthe resulting residue was purified by silica gel column chromatography (chloroform-MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-4e31b68b89a2401bbc988e2a880062c6
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263607B2

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