Aluminium lithium hydride → rac-tert-butyl N-[(1r,4r)-4-formylcyclohexyl]carbamate

HRID 29759

Reaktionsgleichung

Reaktionsgleichung von HRID 29759
[C:1]([O:5][C:6](=[O:20])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:19])N(OC)C)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[C:1]([O:5][C:6](=[O:20])[NH:7][CH:8]1[CH2:9][CH2:10][CH:11]([CH:14]=[O:19])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 24720928Tert-butyl trans-4-(N-methoxy-N-methylcarbamoyl)cyclohexylcarbamate

Produkt 1

HCID 11020615rac-tert-butyl N-[(1r,4r)-4-formylcyclohexyl]carbamateAusbeute 105,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

[4-(Methoxy-methyl-carbamoyl)-cyclohexyl]-carbamic acid tert-butyl ester (7.50 g, 26.2 mmol) in dry ether (150 ml) was reduced with an excess LiAlH4. The reaction mixture was quenched by careful addition of water and extracted with CHCl3. The mixture was dried and concentrated under reduced pressure to give (4-formyl-cyclohexyl)-carbamic acid tert-butyl ester (6.30 g, 93%).

Aufarbeitung

  1. customThe reaction mixture was quenched by careful addition of water
  2. extractionextracted with CHCl3
  3. customThe mixture was dried
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4957361cdce74dd4a55bb646c85e54e8
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423012B2

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