Ammonium Chloride → HCID 86647903, Verbindung

HRID 574925Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 574925
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:4][CH2:3]1.[CH3:17][Li].[NH4+].[Cl-]>O1CCCC1.CCOCC>[OH:1][C:2]1([CH3:17])[CH2:3][CH2:4][CH:5]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[CH2:6][CH2:7]1

Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 404240274-(Aminomethyl)cyclohexanone, N-BOC protectedHCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 86647903HCID 86647903, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a vigorous stirring solution of tert-butyl (4-oxocyclohexyl)methylcarbamate (1.7 g) in tetrahydrofuran (40 mL) at −78° C. was dropwise added 1.6 M methyllithium (14.02 mL) in ether. After completion of the addition, the mixture was stirred at −78° C. for 1.2 hours and poured into a cold NH4Cl aqueous solution. The resulting mixture was extracted with dichloromethane (100 ml, three times) and the organic layer was dried over Na2SO4, filtered, and concentrated. The residue was dissolved in dichloromethane and loaded onto an Analogix purification system, and it was eluted with 0-50% ethyl acetate in dichloromethane to provide the title compound.

Aufarbeitung

  1. customat −78° C.
  2. additionAfter completion of the addition
  3. extractionThe resulting mixture was extracted with dichloromethane (100 ml, three times)
  4. dry with materialthe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in dichloromethane
  8. customloaded onto an Analogix purification system, and it
  9. washwas eluted with 0-50% ethyl acetate in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-5eede4a3277f408da14eaba07a4751f3
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034875B2

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