Acetic Acid → HCID 22593733, Verbindung

HRID 225865

Reaktionsgleichung

Reaktionsgleichung von HRID 225865
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1C=O.[CH:13]1([NH2:16])[CH2:15][CH2:14]1.C(O)(=O)C.[BH3-]C#N.[Na+]>CO>[CH:13]1([NH:16][C:3]2[N:2]([CH3:1])[C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:15][CH2:14]1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 69828CyclopropylamineHCID 2671641-Methylindole-2-carboxaldehydeHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 22593733HCID 22593733, VerbindungAusbeute 69,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 1-methylindole-2-carboxaldehyde (1.5 g, 10 mmole), cyclopropylamine (1.14 g, 20 mmole), and glacial acetic acid (0.6 mL, 10 mmole) in MeOH (30 mL) was added NaBH3CN (0.69 g, 11 mmole). The reaction was stirred at RT overnight, then was concentrated in vacuo. The residue was diluted with 10% NaOH and extracted with CH2Cl2. The combined organic extracts were washed with brine, dried over MgSO4, and concentrated. Flash chromatography on silica gel (3% MeOWCH2Cl2) gave the title compound (1.3 g. 65%) as a semi-solid: MS (ES) m/e 201 (M+H)+.

Aufarbeitung

  1. concentrationwas concentrated in vacuo
  2. additionThe residue was diluted with 10% NaOH
  3. extractionextracted with CH2Cl2
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c494e2b36f35435db665985ce581a063
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557125B2

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