Aluminium lithium hydride → HCID 178486030, compound

HRID 25593Notes

Reaction equation

HRID 25593 reaction equation
C([O:3][C:4](=O)[CH:5]=[CH:6][CH2:7][CH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH3:16])[CH2:11][CH2:10]1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CO.C1COCC1.[Pd]>[C:20]([O:19][C:17](=[O:18])[N:15]([C@H:12]1[CH2:11][CH2:10][C@H:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][OH:3])[CH2:14][CH2:13]1)[CH3:16])([CH3:21])([CH3:23])[CH3:22]

Participants

6

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178471411HCID 178471411, compound

Product 1

HCID 178486030HCID 178486030, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.45 g (7.2 mmol) trans-5-[4-(tert-Butoxycarbonyl-methyl-amino)-cyclohexyl]-pent-2-enoic acid ethyl ester and 200 mg of Pd/C (10%) in 40 ml MeOH was stirred for 20 h under H2-atmosphere. After filtration and evaporation of the methanol under vacuo, 2.39 g 5-[4-(tert-Butoxy carbonyl-methyl-amino)-cyclohexyl]-pentanoic acid ethyl ester could be isolated. 2.05 g (6.0 mmol) of this ester and 470 mg (12 mmol) of LiAlH4 were stirred in 20 ml of THF at RT for 5 h. Exess of LiAlH4 was destroyed by adding 10 ml of EtOAc and by carefully dropping brine to the reaction-mixture. The solution was dissolved in ether and washed with 1N HCl and water. The organic phase was concentrated under reduced pressure yielding 1.75 g (97%) of clean trans-[4-(5-Hydroxy pentyl)-cyclohexyl)-methyl-carbamic acid tert-butyl ester, MS: 300 (MH+).

Workup

  1. filtrationAfter filtration and evaporation of the methanol under vacuo, 2.39 g 5-[4-(tert-Butoxy carbonyl-methyl-amino)-cyclohexyl]-pentanoic acid ethyl ester
  2. customcould be isolated
  3. customExess of LiAlH4 was destroyed
  4. additionby adding 10 ml of EtOAc
  5. dissolutionThe solution was dissolved in ether
  6. washwashed with 1N HCl and water
  7. concentrationThe organic phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2700b0e304674bb0a4cc8cbdf0e04885
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

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