Aluminium lithium hydride → HCID 20031090, compound

HRID 232149Notes

Reaction equation

HRID 232149 reaction equation
C([O:3][C:4]([C:6]1[C:10]2[CH2:11][CH2:12][CH2:13][C:9]=2[N:8]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:7]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:14]([N:8]1[C:9]2[CH2:13][CH2:12][CH2:11][C:10]=2[C:6]([CH2:4][OH:3])=[N:7]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54375111HCID 54375111, compound

Product 1

HCID 20031090HCID 20031090, compoundYield 1,065.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-benzyl-1,4,5,6-tetrahydro-3-cyclopentapyrazole carboxylic acid ethyl ester (6.0 g, 2.22 mmol) in THF (125 ml) was treated with lithium aluminum hydride (1.73 g, 44.4 mmol) and reacted at ambient temperature for 3.5 hours. Excess reagent was quenched with 10% aqueous THF (18 ml), 15% sodium hydroxide (5.4 ml) and water (5.4 ml). The mixture was diluted with ethyl acetate and filtered. The filtrate was washed with 5% brine solutions, dried, and evaporated to provide the title compound (5.40 g) as an oil.

Workup

  1. customreacted at ambient temperature for 3.5 hours
  2. customExcess reagent was quenched with 10% aqueous THF (18 ml), 15% sodium hydroxide (5.4 ml) and water (5.4 ml)
  3. additionThe mixture was diluted with ethyl acetate
  4. filtrationfiltered
  5. washThe filtrate was washed with 5% brine solutions
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-ba1834a51b864f498493990d2345a5a1
Source dataset
uspto-grants-1989_07
Patent number
US04851425

Reaction notes

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