Citric Acid → 1-Benzyl-2-(1-hydroxyethyl)-4-methoxy-6,7,8,9-tetrahydro-1h-benz[g]indole

HRID 489111Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 489111
[C:1]([C:4]1[N:5]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:6]2[C:11]([CH:12]=1)=[C:10]([O:13][CH3:14])[CH:9]=[C:8]1[CH2:15][CH2:16][CH2:17][CH2:18][C:7]=21)(=[O:3])[CH3:2].[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[CH2:19]([N:5]1[C:6]2[C:11](=[C:10]([O:13][CH3:14])[CH:9]=[C:8]3[CH2:15][CH2:16][CH2:17][CH2:18][C:7]3=2)[CH:12]=[C:4]1[CH:1]([OH:3])[CH3:2])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Komponenten

5

Edukt 3

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 114730712-Acetyl-1-benzyl-4-methoxy-6,7,8,9-tetrahydro-1h-benz[g]indole

Produkt 1

HCID 114731251-Benzyl-2-(1-hydroxyethyl)-4-methoxy-6,7,8,9-tetrahydro-1h-benz[g]indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2-acetyl-1-benzyl-4-methoxy-6,7,8,9-tetrahydro-1H-benz[g]indole (4.68 g, 14.0 mmol) in ethanol (50 mL) was added sodium borohydride (537 mg, 14.0 mmol). After stirring for 2 h, 10% aqueous citric acid (10 mL) was added and the mixture concentrated in vacuo. The residue was dissolved in ethyl acetate, washed once with water, and once with saturated sodium bicarbonate solution. The organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo to provide the title compound in quantitative yield. 1H NMR (CDCl3) δ 7.20 (m, 3H), 6.79 (d, J=7.0 Hz, 2H), 6.65 (s, 1H), 6.24 (s, 1H), 5.76 (s, 2H), 4.75 (quintet, J=6.6 Hz, 1H), 3.91 (s, 3H), 2.97 (m, 1H), 2.84 (m, 3H), 1.70 (m, 4H), 1.60 (d, J=6.6 Hz, 3H); MS ES+ m/e 336 (p+1).

Aufarbeitung

  1. concentrationthe mixture concentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed once with water
  4. dry with materialThe organic layer was dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-752f0f9d91f947a5a7e11ac961c71da0
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06974831B2

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