Sodium Hydroxide → HCID 70608931, compound

HRID 426765Notes

Reaction equation

HRID 426765 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH:13]2[CH:21]3[CH:17]([CH2:18][NH:19][CH2:20]3)[CH2:16][C:15]3[CH:22]=[CH:23][CH:24]=[CH:25][C:14]2=3)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:26]1[CH2:28][CH:27]1[C:29](N)=O.[OH-].[Na+]>O1CCCC1>[CH:27]1([CH2:29][N:19]2[CH2:18][CH:17]3[CH:21]([CH:13]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)[C:14]4[CH:25]=[CH:24][CH:23]=[CH:22][C:15]=4[CH2:16]3)[CH2:20]2)[CH2:28][CH2:26]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 70609535HCID 70609535, compound

Product 1

HCID 70608931HCID 70608931, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 g of lithium aluminium hydride is added portionwise to a warm solution of 8.6 g of (3aRS,4SR,9aSR)-3a,4,9,9a-tetrahydro-4-phenyl-benz[f]-isoindoline-2-cyclopropylcarboxylic acid amide in 100 cc of tetrahydrofuran. The mixture is stirred at room temperature for 1 hour, is then decomposed with a 2 N caustic soda solution and filtered. The concentrated filtrate is reduced to a paste with silica gel in benzene/ethyl acetate (1:1), filtration and concentration by evaporation are effected, whereby the title compound, having a M.P. of 65-68° (after crystallization from pentane), is obtained.

Workup

  1. filtrationfiltered
  2. filtrationThe concentrated filtrate is reduced to a paste with silica gel in benzene/ethyl acetate (1:1), filtration and concentration by evaporation
  3. customa M.P. of 65-68° (after crystallization from pentane)
  4. customis obtained

Sources & evidence

ORD record
ord-c0efb726cb7d4279952a9b34daafaddd
Source dataset
uspto-grants-1979_10
Patent number
US04171369

Reaction notes

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