Sodium cyanoborohydride → Methyl 1-butylindoline-6-carboxylate

HRID 348950

Reaktionsgleichung

Reaktionsgleichung von HRID 348950
[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-81d413419b194d14aaa1bfcd4e6852e6
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176242B2

Verknüpfte Notizen

Wird geladen…