Sodium Sulfate → 3-Amino-8-t-butyl-1-oxaspiro(4,5)-decane

HRID 232555Notes

Reaction equation

HRID 232555 reaction equation
[C:1]([CH:5]1[CH2:16][CH2:15][C:8]2([O:12][CH2:11][C:10](=[N:13]O)[CH2:9]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[NH2:13][CH:10]1[CH2:9][C:8]2([CH2:7][CH2:6][CH:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:16][CH2:15]2)[O:12][CH2:11]1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydride2×HCID 86750119HCID 86750119, compound

Product 1

HCID 190401633-Amino-8-t-butyl-1-oxaspiro(4,5)-decaneYield 76.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

8-t-Butyl-1-oxaspiro(4,5)-decane-3-one oxime (17.5 g, 76 mmol) in tetrahydrofuran (50 ml) was added to a solution of lithium- aluminium hydride (4.5 g, 0.125 mol) in tetrahydrofuran (100 ml). The reaction mixture was refluxed for 4 hours, cooled end excess LAH was hydrolysed by addition of saturated aqueous sodium sulfate. solids were filtered off washed with tetrahydrofuran and the solvent was stripped off in vacuo. Kugelrohr distillation of the resulting pale yellow oil (16.9 g) gave a colourless oil (12.3 g) Bp.: 125° C./0.02 mbar, nD22 :1.4840.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. filtrationsolids were filtered off
  3. washwashed with tetrahydrofuran
  4. distillationKugelrohr distillation of the resulting pale yellow oil (16.9 g)

Sources & evidence

ORD record
ord-913d502fa58b48bdb6c8b03c29b3ab54
Source dataset
uspto-grants-1997_01
Patent number
US05591741

Reaction notes

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