Water → 4-Amino-1,3,3a,4,7,7a-hexahydro-isoindole

HRID 129424Notes

Reaction equation

HRID 129424 reaction equation
C(OC([NH:8][CH:9]1[CH:17]=[CH:16][CH2:15][CH:14]2[CH:10]1[C:11](=O)[NH:12][C:13]2=O)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>FC(F)(F)C(O)=O.O1CCCC1>[NH2:8][CH:9]1[CH:17]=[CH:16][CH2:15][CH:14]2[CH:10]1[CH2:11][NH:12][CH2:13]2

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 193714494-(Tert.-butyloxycarbonylamino)-1,3-dioxo-1,3,3a,4,7,7a-hexahydroisoindoleHCID 21226445Aluminium lithium hydride

Product 1

HCID 152832494-Amino-1,3,3a,4,7,7a-hexahydro-isoindole

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

13.3 g (50 mmol) of 4-tert.-butyloxycarbonylamino-1,3-dioxo-1,3,3a,4,7,7a-hexahydro-isoindole (from Example Z23, method II) are stirred overnight at room temperature in 166 ml of trifluoroacetic acid. The trifluoroacetic acid is then distilled off at 10 mbar, and the residue is freed from remaining acid in a high vacuum at 50° C. The residue is subsequently taken up in absolute tetrahydrofuran and concentrated in vacuo. The residue is taken up in 100 ml of absolute tetrahydrofuran and the mixture is added dropwise under nitrogen to a solution of 11.3 g (0.3 mol) of lithium aluminium hydride in 300 ml of absolute tetrahydrofuran. The mixture is then refluxed for 16 hours. 11.3 g of water in 34 ml of tetrahydrofuran, 11.3 ml of 10% strength sodium hydroxide solution and 34 ml of water are added dropwise in succession to the cold mixture. The precipitate is filtered off with suction and washed with tetrahydrofuran. The filtrate is concentrated, and the residue is distilled.

Workup

  1. distillationThe trifluoroacetic acid is then distilled off at 10 mbar
  2. customat 50° C
  3. concentrationconcentrated in vacuo
  4. temperatureThe mixture is then refluxed for 16 hours
  5. filtrationThe precipitate is filtered off with suction
  6. washwashed with tetrahydrofuran
  7. concentrationThe filtrate is concentrated
  8. distillationthe residue is distilled

Sources & evidence

ORD record
ord-d5143bddb73f4f73932db5b10f919d77
Source dataset
uspto-grants-1995_11
Patent number
US05468742

Reaction notes

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