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

HRID 227930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 227930
[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 702EthanolLösungsmittel2×

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 washed with diethylether (500 mL), followed by addition of concentrated hydrochloric acid to adjust the pH to 1. The resulting crystals were filtrated, washed with water, dried under reduced pressure to give 4-benzyloxycarbonylaminobicyclo[2.2.2]octane-1-carboxylic acid (56.1 g).

Aufarbeitung

  1. customwas evaporated under reduced pressure
  2. washthe residue 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-b3a6c75725424e96b373d982a3f2e797
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560569B2

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