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Lithium borohydride → 1,1-Dimethylethyl 6-cyano-1-(2-hydroxyethyl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

HRID 2383314
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2383314
C([O:5][C:6](=O)[CH2:7][CH:8]1[C:17]2[C:12](=[C:13]([CH3:20])[C:14]([C:18]#[N:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10][N:9]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])CCC.[BH4-].[Li+]>C(O)C.C(OCC)C>[C:18]([C:14]1[C:13]([CH3:20])=[C:12]2[C:17](=[CH:16][CH:15]=1)[CH:8]([CH2:7][CH2:6][OH:5])[N:9]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH2:10][CH2:11]2)#[N:19]
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Komponenten

5

Edukt 2

HCID 4148881Lithium borohydrideHCID 595910861,1-Dimethylethyl 1-[2-(butyloxy)-2-oxoethyl]-6-cyano-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Produkt 1

HCID 595910851,1-Dimethylethyl 6-cyano-1-(2-hydroxyethyl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylateAusbeute 96,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel
HCID 3283
Diethyl Ether
Lösungsmittel

Versuchsvorschrift

To a solution of 1,1-dimethylethyl 1-[2-(butyloxy)-2-oxoethyl]-6-cyano-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 18; 2.15 g, 5.56 mmol) in ethanol (10 ml) and diethyl ether (40 ml) was added lithium borohydride (2M solution in tetrahydrofuran, 4.17 ml; 8.34 mmol) at 25° C. under nitrogen. After 1.5 h at 25° C., the solvent was removed, and the residue dissolved in ethyl acetate. The solution was washed with 1N hydrochloric acid, and the aqueous layer further extracted with ethyl acetate. The combined organic phases were washed with saturated sodium bicarbonate, dried over MgSO4 and concentrated in vacuo to give the title compound (1.70 g) as a white foam.

Aufarbeitung

  1. customthe solvent was removed
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe solution was washed with 1N hydrochloric acid
  4. extractionthe aqueous layer further extracted with ethyl acetate
  5. washThe combined organic phases were washed with saturated sodium bicarbonate
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-69a402ed1e9840edb9fe71de1cf2eb9b
Quelldatensatz
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08263620B2

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