5-Methoxyindole → 5-methoxy-2,3-dihydro-1H-indole

HRID 624038

Reaktionsgleichung

Reaktionsgleichung von HRID 624038
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.C([BH3-])#N.[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6]2

Komponenten

4

Edukt 2

HCID 138725-MethoxyindoleHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 107019745-methoxy-2,3-dihydro-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 5-methoxyindole (500 mg, 3.39 mmol) in acetic acid (34 mL), sodium cyanoborohydride (641 mg, 10.20 mmol) was added in portions. After stirring for 30 min at rt, the mixture was quenched with water (2.0 mL) and concentrated. The yellow residue was dissolved in DCM, washed with aq. sat. NaHCO3-solution and brine. The org. layers was dried (MgSO4), filtered and the solvent removed under reduced pressure to yield 5-methoxyindoline which was stored in the freezer. LC-MS conditions B: tR=0.24 min, [M+H]+=150.09.

Aufarbeitung

  1. customthe mixture was quenched with water (2.0 mL)
  2. concentrationconcentrated
  3. dissolutionThe yellow residue was dissolved in DCM
  4. washwashed with aq. sat. NaHCO3-solution and brine
  5. dry with materiallayers was dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-79a21aeeab26494e803fecfef70fd1ca
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303023B2

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