Water → HCID 15283247, compound

HRID 128515Notes

Reaction equation

HRID 128515 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O[C:12]([NH:14][CH:15]1[CH:23]=[CH:22][CH2:21][CH:20]2[CH:16]1[C:17](=O)[NH:18][C:19]2=O)=O)(C)(C)C.O.[OH-].[Na+]>O1CCCC1>[CH3:12][NH:14][CH:15]1[CH:23]=[CH:22][CH2:21][CH:20]2[CH:16]1[CH2:17][NH:18][CH2:19]2

Participants

6

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 15283247HCID 15283247, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

27.1 g (0.71 mol) of lithium aluminium hydride in 300 ml of absolute tetrahydrofuran are initially introduced into the reaction vessel, under nitrogen, and a solution of 57 g (0.21 mol) of 4-(tert.-butyloxycarbonylamino)-1,3-dioxo-1,3,3a,4,7,7a-hexahydroisoindole in 570 ml of absolute tetrahydrofuran is added dropwise. The mixture is then boiled under reflux cooling overnight. After cooling, 27.1 g of water in 82 ml of tetrahydrofuran, 27.1 g of 10% strength sodium hydroxide solution and 81.3 g of water are added dropwise to the batch in succession. The salts are filtered off with suction and washed with tetrahydrofuran and the filtrate is concentrated in vacuo. The residue is distilled under a high vacuum.

Workup

  1. temperatureunder reflux
  2. temperaturecooling overnight
  3. temperatureAfter cooling
  4. filtrationThe salts are filtered off with suction
  5. washwashed with tetrahydrofuran
  6. concentrationthe filtrate is concentrated in vacuo
  7. distillationThe residue is distilled under a high vacuum

Sources & evidence

ORD record
ord-753d10e1eb004120847b35c4a77f353c
Source dataset
uspto-grants-1995_11
Patent number
US05464796

Reaction notes

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