Methanol → Methyl 4-(1-aminocyclopropyl)benzoate

HRID 2359980

Reaktionsgleichung

Reaktionsgleichung von HRID 2359980
[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 451402084-(1-Aminocyclopropyl)benzoic acid

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. Step 2:

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-92df5fd8102e4f8296f941332cc75bf8
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08686018B2

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