methyl 1H-indole-5-carboxylate → methyl 2,3-dihydro-1H-indole-5-carboxylate

HRID 84185

Reaktionsgleichung

Reaktionsgleichung von HRID 84185
C([BH3-])#N.[Na+].[NH:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1>CC(O)=O>[CH3:17][O:16][C:14]([C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[NH:5][CH2:6][CH2:7]2)=[O:15]

Komponenten

4

Edukt 2

HCID 2737635methyl 1H-indole-5-carboxylateHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 21782110methyl 2,3-dihydro-1H-indole-5-carboxylateAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

sodium cyanoborohydride (0.16 g, 2.57 mmol) was added to a solution of methyl indole-5-carboxylate (9) (0.30 g, 1.71 mmol) in AcOH (2 mL) at 0° C. The reaction mixture was warmed to room temperature and stirred for 2 h before it was quenched with water at 0° C. Concentrated NaOH was added to reach pH=10. The aqueous layer was extracted with CH2Cl2 (15 mL×3). The combined organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure to give a yellow residue, which was purified by silica gel chromatography (EtOAc:n-hexane=1:2) to afford 10 (0.28 g). 1H NMR (500 MHz, CDCl3): δ 3.06 (t, J=8.5 Hz, 2H), 3.65 (t, J=8.5 Hz, 2H), 3.84 (s, 3H), 6.53-6.55 (m, 1H), 7.75-7.76 (m, 2H).

Aufarbeitung

  1. customwas quenched with water at 0° C
  2. additionConcentrated NaOH was added
  3. extractionThe aqueous layer was extracted with CH2Cl2 (15 mL×3)
  4. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow residue, which
  7. customwas purified by silica gel chromatography (EtOAc:n-hexane=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-96e6d38a98f94056932ea4acec23252c
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846748B2

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