Aluminium lithium hydride → HCID 178483640, compound

HRID 967213Notes

Reaction equation

HRID 967213 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12](=[O:26])[N:13]([CH3:25])[CH2:14][CH2:15][C@H:16]1[CH2:21][CH2:20][C@H:19]([CH2:22][CH:23]=[O:24])[CH2:18][CH2:17]1)([CH3:10])([CH3:9])[CH3:8]>O1CCCC1.[Cl-].[Na+].O>[C:7]([O:11][C:12](=[O:26])[N:13]([CH2:14][CH2:15][C@H:16]1[CH2:17][CH2:18][C@H:19]([CH2:22][CH2:23][OH:24])[CH2:20][CH2:21]1)[CH3:25])([CH3:8])([CH3:10])[CH3:9]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178483639HCID 178483639, compound

Product 1

HCID 178483640HCID 178483640, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

800 mg (21 mmol) of lithium aluminium hydride were added within 10 minutes to a solution of 4.5 g (15.87 mmol) crude trans-methyl-{2-[4-(2-oxo-ethyl)-cyclohexyl]-ethyl}-carbamic acid tert-butyl ester in 40 ml of tetrahydrofuran. After stirring for 3 hours at room temperature, 40 ml of brine was dropped carefully into the reaction mixture. The reaction mixture was stirred for another 20 minutes at room temperature and then partitioned between ether, 1N HCl and water. After drying of the ether phase over sodium sulfate and concentration under reduced pressure, 4.26 g of trans-{2-[4-(2-hydroxy-ethyl)-cyclohexyl]-ethyl}-methyl-carbamic acid tert-butyl ester was obtained, which was used without further purification.

Workup

  1. stirringThe reaction mixture was stirred for another 20 minutes at room temperature
  2. custompartitioned between ether, 1N HCl and water
  3. dry with materialAfter drying of the ether phase over sodium sulfate and concentration under reduced pressure

Sources & evidence

ORD record
ord-0d5eb9a847554dbeaeaabf614597a09f
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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