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

HRID 335134Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 335134
[CH3:1][CH:2]1[CH2:6][CH2:5][C:4](=O)[C@@H:3]1[C:8]([O:10][CH2:11][CH3:12])=[O:9].C([O-])(=O)C.[NH4+:17]>CO>[NH2:17][C:4]1[CH2:5][CH2:6][C@@H:2]([CH3:1])[C:3]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

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

To a solution of (R)-ethyl 2-methyl-5-oxocyclopentanecarboxylate (106 g, 622 mmol) in 1.2 L MeOH was added ammonium acetate (240 g, 3.1 mol). The reaction was stirred for 20 hours and concentrated to remove MeOH. The resulting residue was dissolved in CH2Cl2, washed with H2O, brine, dried (Na2SO4), filtered and concentrated to give the title compound (102 g, 97% yield) as an orange oil.

Aufarbeitung

  1. concentrationconcentrated
  2. customto remove MeOH
  3. dissolutionThe resulting residue was dissolved in CH2Cl2
  4. washwashed with H2O, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-122c841efaae456684147e46f8cacd1d
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883828B2

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