Methanol → Methyl 4-(1-aminocyclopropyl)benzoate

HRID 1466405

Reaktionsgleichung

Reaktionsgleichung von HRID 1466405
[NH2:1][C:2]1([C:5]2[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=2)[CH2:4][CH2:3]1.CO.[CH3:16][Si](C=[N+]=[N-])(C)C.CCCCCC>C1COCC1>[NH2:1][C:2]1([C:5]2[CH:13]=[CH:12][C:8]([C:9]([O:11][CH3:16])=[O:10])=[CH:7][CH:6]=2)[CH2:4][CH2:3]1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 8058HexaneHCID 167693TrimethylsilyldiazomethaneHCID 45140208HCID 45140208, Verbindung

Produkt 1

HCID 45140209Methyl 4-(1-aminocyclopropyl)benzoateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-(1-aminocyclopropyl)benzoic acid (1.75 g, 0.00988 mol) was stirred in THF (20 mL) and Methanol (10 mL) over ice/water bath. 2.00 M of trimethylsilyldiazomethane in hexane (9.9 mL, 0.020 mol) was added and the mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated down to viscous oil which solidified upon standing to give a crystalline solid. Crude material was dried on high vacuum line for 12 hours to give methyl 4-(1-aminocyclopropyl)benzoate (1.65 g, 87%) as pale brown solid.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated down to viscous oil which
  2. customto give a crystalline solid
  3. customCrude material was dried on high vacuum line for 12 hours

Quellen und Nachweise

ORD-Eintrag
ord-7407d88d941c48b0880db251dbbbc6b4
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000024B2

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