Water → HCID 15283247, compound

HRID 129423Notes

Reaction equation

HRID 129423 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

Under nitrogen, 27.1 g (0.71 mol) of lithium aluminium hydride are introduced into 300 ml of absolute tetrahydrofuran, 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 refluxed overnight. 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 then added dropwise to the cold batch. The salts are filtered off with suction and washed with tetrahydrofuran, and the filtrate is concentrated in vacuo. The residue is distilled off under a high vacuum.

Workup

  1. temperatureThe mixture is then refluxed overnight
  2. filtrationThe salts are filtered off with suction
  3. washwashed with tetrahydrofuran
  4. concentrationthe filtrate is concentrated in vacuo
  5. distillationThe residue is distilled off under a high vacuum

Sources & evidence

ORD record
ord-70bfb5559a6b47cab6b5379f3d7dfbf2
Source dataset
uspto-grants-1995_11
Patent number
US05468742

Reaction notes

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