Sodium Hydroxide → 4-(Benzyloxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylic acid

HRID 555673Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 555673
[CH2:1]([O:8][C:9]([NH:11][C:12]12[CH2:19][CH2:18][C:15]([C:20]([O:22]C)=[O:21])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH2:1]([O:8][C:9]([NH:11][C:12]12[CH2:19][CH2:18][C:15]([C:20]([OH:22])=[O:21])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 23149677Methyl 4-{[(benzyloxy)carbonyl]amino}bicyclo[2.2.2]octane-1-carboxylate

Produkt 1

HCID 106622014-(Benzyloxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylic acidAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Methyl 4-benzyloxycarbonylaminobicyclo[2.2.2]octane-1-carboxylate (64.3 g) was dissolved in ethanol (1100 mL). To this solution, a 1 mol/L aqueous solution of sodium hydroxide (1000 mL) was added and the mixture was stirred at 50° C. for 1 hour. Ethanol in the mixture was evaporated under reduced pressure and the residue was washed with diethylether (500 mL), followed by addition of concentrated hydrochloric acid to adjust the pH to acidic (pH 1). The resulting crystals were filtrated, washed with water, and dried under reduced pressure to give 4-benzyloxycarbonylaminobicyclo[2.2.2]octane-1-carboxylic acid (56.1 g).

Aufarbeitung

  1. customEthanol in the mixture was evaporated under reduced pressure
  2. washthe residue was washed with diethylether (500 mL)
  3. additionfollowed by addition of concentrated hydrochloric acid
  4. filtrationThe resulting crystals were filtrated
  5. washwashed with water
  6. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-aad614e5dd1b4d36b475426b42923532
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08053465B2

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