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

HRID 29759

Reaction equation

HRID 29759 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 11020615rac-tert-butyl N-[(1r,4r)-4-formylcyclohexyl]carbamateYield 105.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

[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%).

Workup

  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

Sources & evidence

ORD record
ord-4957361cdce74dd4a55bb646c85e54e8
Source dataset
uspto-grants-2008_09
Patent number
US07423012B2

Linked notes

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