Aluminium lithium hydride → HCID 178486036, compound

HRID 25622Notes

Reaction equation

HRID 25622 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][CH2:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH3:15])[CH2:10][CH2:9]1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:19]([O:18][C:16](=[O:17])[N:14]([C@H:11]1[CH2:10][CH2:9][C@H:8]([CH2:7][CH2:6][CH2:5][CH2:4][OH:3])[CH2:13][CH2:12]1)[CH3:15])([CH3:20])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178471461HCID 178471461, compound

Product 1

HCID 178486036HCID 178486036, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.57 g (4.82 mmol) 4-[4-(tert-Butoxycarbonyl-methyl-amino)-cyclohexyl]-but-2-enoic acid ethyl ester and 200 mg of Pd/C (10%) in 20 ml of MeOH was stirred at RT under H2-atmosphere for 3 h. After filtration, the solution was concentrated under reduced pressure to dryness, to give 1.58 g of clean trans-4-[4-(tert-Butoxycarbonyl-methyl-amino)-cyclohexyl]-butyric acid ethyl ester. 1.58 g (4.82 mmol) trans-4-[4-(tert-Butoxycarbonyl-methyl-amino)-cyclohexyl]-butyric acid ethyl ester in 20 ml of THF, was treated at RT with 390 mg of LiAlH4. After stirring the solution for 30 min at RT, the excess of LiAH4 was destroyed by adding dropwise 10 ml of saturated brine under ice-cooling. The reaction mixture was partitioned between Et2O/1M HCl and H2O. The ether-solution was concentrated in vacuo, to give 1.37 g (99%) of pure trans-[4-(4-Hydroxy-butyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester.

Workup

  1. customthe excess of LiAH4 was destroyed
  2. additionby adding dropwise 10 ml of saturated brine under ice-
  3. temperaturecooling
  4. customThe reaction mixture was partitioned between Et2O/1M HCl and H2O
  5. concentrationThe ether-solution was concentrated in vacuo

Sources & evidence

ORD record
ord-24001a92c03844e0a5818e50c3c94f26
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

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