Sodium cyanoborohydride → Methyl 1-butylindoline-6-carboxylate

HRID 14159

Reaktionsgleichung

Reaktionsgleichung von HRID 14159
[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=2)[CH:7]=[CH:6]1)[CH2:2][CH2:3][CH3:4].C([BH3-])#N.[Na+]>C(O)(=O)C>[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=2)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]

Komponenten

4

Edukt 2

HCID 5003444Sodium cyanoborohydrideHCID 21086134methyl 1-butyl-1H-indole-6-carboxylate

Produkt 1

HCID 21086137Methyl 1-butylindoline-6-carboxylateAusbeute 77,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a mixture of methyl 1-butyl-1H-indole-6-carboxylate, (2.1 g) in glacial acetic acid (25 mL) was added sodium cyanoborohydride (2.28 g). The mixture was heated at 40° C. for 3 h then cooled to room temperature, partitioned between water and ethyl acetate and the layers were separated. The organic layer was washed three times with brine, dried over anhydrous sodium sulfate and concentrated to give 1.64 g of the title compound: 1H NMR (CDCl3) δ 0.969, 1.43, 1.59, 2.99, 3.1, 3.4, 3.88, 7.07, 7.34.

Aufarbeitung

  1. temperaturethen cooled to room temperature
  2. custompartitioned between water and ethyl acetate
  3. customthe layers were separated
  4. washThe organic layer was washed three times with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ec36e4517aeb4f9583456d798cf68415
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

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