Cyclopentanone → 3-Cyclopentylamino-2,2-dimethyl-propanoic acid methyl ester

HRID 2111256Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2111256
[CH3:1][O:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][NH2:6].[C:10]1(=O)[CH2:14][CH2:13][CH2:12][CH2:11]1.C([O-])(=O)C.[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH3:1][O:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][NH:6][CH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1

Komponenten

6

Edukt 4

HCID 8452CyclopentanoneHCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 13285789Methyl 3-amino-2,2-dimethylpropanoate

Produkt 1

HCID 576350433-Cyclopentylamino-2,2-dimethyl-propanoic acid methyl esterAusbeute 95,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 21.98 g (0.167 mole) of 3-amino-2,2-dimethyl-propanoic acid methyl ester (from method 6) in 500 mL of dichloromethane cooled to 0 degrees, was added 14.1 g (0.167 mole) of cyclopentanone, 16.0 g (0.181 mole) of sodium acetate and 52.0 g (0.025 mole) of sodium triacetoxyborohydride. The mixture stirred at room temp. for 22 hours, and then quenched by the addition of 500 mL of saturated sodium bicarbonate solution. The mixture was stirred for 1 hour and then extracted twice 400 mL of dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 31.8 g of 3-cyclopentylamino-2,2-dimethyl-propanoic acid methyl ester which was used without further purification.

Aufarbeitung

  1. customquenched by the addition of 500 mL of saturated sodium bicarbonate solution
  2. stirringThe mixture was stirred for 1 hour
  3. extractionextracted twice 400 mL of dichloromethane
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2bf9a22d74014e8a8d07086cc1a588d1
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07517873B2

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