Aluminium lithium hydride → HCID 86736136, compound

HRID 1703573Notes

Reaction equation

HRID 1703573 reaction equation
C(O[C:4]([N:6]1[CH:14]2[CH:9]([C:10]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)([OH:15])[CH2:11][CH2:12][CH2:13]2)[CH2:8][CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([C:10]2([OH:15])[CH2:11][CH2:12][CH2:13][CH:14]3[CH:9]2[CH2:8][CH2:7][N:6]3[CH3:4])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86736137HCID 86736137, compound

Product 1

HCID 86736136HCID 86736136, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

15 g of (3aRS, 4SR, 7aRS)-4-p-chlorophenyl-hexahydro-4-hydroxy-1-indoline carboxylic acid ethyl ester and 4 g of lithium aluminum hydride in 100 ml of tetrahydrofuran were heated at reflux for 15 hours. Any remaining lithium aluminum hydride was destroyed by the addition of water. Partition between water and diethyl ether afforded after separation and working up of the organic phase the title compound as an oil (M.P. of the face base from diethyl ether/petroleum ether 98°-101°).

Workup

  1. temperatureat reflux for 15 hours
  2. customAny remaining lithium aluminum hydride was destroyed by the addition of water
  3. customPartition between water and diethyl ether
  4. customafforded
  5. customafter separation
  6. customfrom diethyl ether/petroleum ether 98°-101°

Sources & evidence

ORD record
ord-e9fad18672a04c07ba8f8b412bc08ed8
Source dataset
uspto-grants-1978_11
Patent number
US04124719

Reaction notes

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