Ammonium Acetate → Ethyl (5R)-2-amino-5-methyl-1-cyclopentene-1-carboxylate

HRID 75394Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 75394
C([O-])(=O)C.[NH4+:5].[CH3:6][CH:7]1[CH2:11][CH2:10][C:9](=O)[C@@H:8]1[C:13]([O:15][CH2:16][CH3:17])=[O:14]>CO>[NH2:5][C:9]1[CH2:10][CH2:11][C@@H:7]([CH3:6])[C:8]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Komponenten

4

Edukt 2

HCID 517165Ammonium AcetateHCID 86618740(R)-ethyl 2-methyl-5-oxocyclopentanecarboxylate

Produkt 1

HCID 59671147Ethyl (5R)-2-amino-5-methyl-1-cyclopentene-1-carboxylateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Ammonium acetate (240 g, 3114 mmol) was added to a solution of (R)-ethyl 2-methyl-5-oxocyclopentanecarboxylate (106.0 g, 622.8 mmol) in MeOH (1.2 L). The reaction mixture was stirred at room temperature under nitrogen for 20 hours, and the reaction was complete as determined by TLC and HPLC. The reaction mixture was concentrated to remove MeOH. The resulting residue was dissolved in DCM, washed with H2O (2×), brine (1×), dried (Na2SO4), filtered, and concentrated to give (R)-ethyl 2-amino-5-methylcyclopent-1-enecarboxylate (102 g, 97% yield) as an oil. LC/MS (APCI+) m/z 170 [M+H]+.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customto remove MeOH
  3. dissolutionThe resulting residue was dissolved in DCM
  4. washwashed with H2O (2×), brine (1×)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-83ad34ccddcd4c8da3f944f7c164697d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835434B2

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