HCID 14793294, compound → HCID 21316300, compound

HRID 1658913Notes

Reaction equation

HRID 1658913 reaction equation
O=[C:2]1[CH2:13][O:12]CC(=O)[NH:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][NH:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[O:12]1[NH:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][NH:3][CH2:2][CH2:13]1

Participants

4

Reactant 2

HCID 14793294HCID 14793294, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21316300HCID 21316300, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 5.0 g. of the diamide obtained in Example 44 in 100 ml. hot anhydrous tetrahydrofuran and 4.8 g. LiAlH4 while stirring over a period of one hour. After the addition is completed, the mixture is stirred under reflux and under a nitrogen atmosphere for eighteen hours. After cooling to room temperature the excess reagent is destroyed by adding a mixture (15 ml.) of water and THF (1.2) followed by 5 ml. NaOH 15% and 15 ml. water. The mixture is filtered and the filtrate is evaporated to dryness. The residue is dissolved in benzene and the solution is passed through a column of Al2O3 with benzene as eluant. The solution is evaporated to dryness and after recrystallization from hot benzene/heptane the desired product is obtained.

Workup

  1. additionA suspension of 5.0 g
  2. additionAfter the addition
  3. temperatureunder reflux and under a nitrogen atmosphere for eighteen hours
  4. customis destroyed
  5. additionby adding a mixture (15 ml.) of water and THF (1.2)
  6. filtrationThe mixture is filtered
  7. customthe filtrate is evaporated to dryness
  8. dissolutionThe residue is dissolved in benzene
  9. customThe solution is evaporated to dryness
  10. customafter recrystallization from hot benzene/heptane the desired product
  11. customis obtained

Sources & evidence

ORD record
ord-01a9cc50f13849f6b120d2bfce7cd6f7
Source dataset
uspto-grants-1976_06
Patent number
US03966766

Reaction notes

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