Acetic Acid → Ethyl (3S, 4aR, 6S, 8aR) 6-(2-cyano-phenylamino)-2-methoxycarbonyl-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate

HRID 583837Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 583837
O=[C:2]1[CH2:11][CH2:10][CH:9]2[CH:4]([CH2:5][CH:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:7]([C:12]([O:14][CH3:15])=[O:13])[CH2:8]2)[CH2:3]1.[NH2:21][C:22]1[CH:29]=[CH:28][CH:27]=[C:26](Cl)[C:23]=1[C:24]#[N:25].C(O)(=O)C.C(=O)(O)[O-].[Na+]>ClCCCl.[Na].CCCCCC.C(OCC)(=O)C.C(OCC)(=O)C>[C:24]([C:23]1[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=1[NH:21][C@H:2]1[CH2:11][CH2:10][C@@H:9]2[C@@H:4]([CH2:5][C@@H:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:7]([C:12]([O:14][CH3:15])=[O:13])[CH2:8]2)[CH2:3]1)#[N:25]

Komponenten

9

Edukt 4

HCID 176Acetic AcidHCID 810562-Amino-6-chlorobenzonitrileHCID 516892Sodium BicarbonateHCID 148779783-Ethyl 2-methyl octahydro-6-oxo-2,3(1H)-isoquinolinedicarboxylate

Produkt 1

HCID 11485962Ethyl (3S, 4aR, 6S, 8aR) 6-(2-cyano-phenylamino)-2-methoxycarbonyl-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylateAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 111,2-DichloroethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 5360545SodiumLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

To a mixture of of ethyl 6-oxo-2-(methoxycarbonyl)-decahydroisoquinoline-3-carboxylate (537 mg, 1.9 mmol), 2-amino-6-chloro-benzonitrile (118 mg, 1.0 mmol), and glacial acetic acid (0.36 mL, 6.0 mmol) in 1,2-dichloroethane (5 mL), sodium triacethoxyborohydride solid (590 mg, 2.8 mmol) was added and the reaction mixture stirred under nitrogen at room temperature for 24 hours. Sodium bicarbonate was added until pH 8, followed by addition of ethyl acetate. The phases were separated and the aqueous phase washed twice with ethyl acetate. The combined organic phases were dried with anhydrous sodium sulfate and concentrated in vacuo. Flash chromatography (silica gel, hexane-ethyl acetate 3:1) afforded 123 mg (32% yield) of the title compound.

Aufarbeitung

  1. additionwas added
  2. customThe phases were separated
  3. washthe aqueous phase washed twice with ethyl acetate
  4. dry with materialThe combined organic phases were dried with anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cede956a332046f59582c33f863d02a2
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06924294B2

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