Sodium Carbonate → HCID 178523817, Verbindung

HRID 25533

Reaktionsgleichung

Reaktionsgleichung von HRID 25533
Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([OH:9])[CH2:5][CH2:4]1.C([O-])([O-])=O.[Na+].[Na+].Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>C1COCC1.O.CCOC(C)=O>[CH2:20]([O:19][C:17](=[O:18])[NH:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([OH:9])[CH2:5][CH2:4]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 178479278HCID 178479278, Verbindung

Produkt 1

HCID 178523817HCID 178523817, VerbindungAusbeute 197,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of 50 g (0.33 mol) trans-4-aminocyclohexanol.hydrochloride and 77 g (0.726 mol, 2.2 eq) Na2CO3 in 650 ml THF and 150 ml water, 51.2 ml (0.363 mol, 1.1 eq) benzyl chloroformate were added at 5° C. over a period of 20 min. The reaction mixture was stirred at RT for 2 h, diluted with EtOAc and the phases were separated. The organic layer was washed with brine, dried over Na2SO4, filtered and evaporated. Trituration from hexane yielded 162.4 g (98%) trans-4-Hydroxy-cyclohexylcarbamic acid benzyl ester as white crystals, MS: 249 (M) (in analogy to: Venuti, Michael C.; Jones, Gordon H.; Alvarez, Robert; Bruno, John J.; J.Med.Chem.; 30; 2; 1987; 303-318).

Aufarbeitung

  1. additionwere added at 5° C. over a period of 20 min
  2. customthe phases were separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f2881ca0ffc24a69967da231ffa7f28e
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858651B2

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