Sodium sulfate decahydrate → 1-(Aminomethyl)-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 467039Notes

Reaction equation

HRID 467039 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:9]1([O:19][Si](C)(C)C)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH2:10]1)#[N:8].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[NH2:8][CH2:7][C:9]1([OH:19])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 117469071-Trimethylsilyloxy-1-cyano-1,2,3,4-tetrahydronaphthaleneHCID 21226445Aluminium lithium hydride

Product 1

HCID 129148591-(Aminomethyl)-1,2,3,4-tetrahydronaphthalen-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of lithium aluminum hydride (12 g, 0.32 mol, 2.25 equivalents) in refluxing THF (150 mL), under a nitrogen atmosphere, was added, dropwise over a period of 30 minutes, a solution of 1-cyano-1-trimethylsilyloxy-1,2,3,4-tetrahydronaphthalene, from Step 1, in 150 mL of THF. The resulting mixture was refluxed for 4 hours and then cooled to ambient temperature and diluted with THF. Sodium sulfate decahydrate was added to quench the excess lithium aluminum hydride. The solids were filtered over Celite® filter aid. The filtrate was then concentrated to give a light brown, waxy solid which was used in the next step without purification.

Workup

  1. additionunder a nitrogen atmosphere, was added, dropwise over a period of 30 minutes
  2. temperatureThe resulting mixture was refluxed for 4 hours
  3. customto quench the excess lithium aluminum hydride
  4. filtrationThe solids were filtered over Celite®
  5. filtrationfilter aid
  6. concentrationThe filtrate was then concentrated
  7. customto give a light brown, waxy solid which
  8. customwas used in the next step without purification

Sources & evidence

ORD record
ord-fb8284a001ff4be3ada36f20b0063b70
Source dataset
uspto-grants-1992_10
Patent number
US05158948

Reaction notes

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