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

HRID 1684690Notes

Reaction equation

HRID 1684690 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. filtrationwere filtered off
  3. washwashed with tetrahydrofuran
  4. distillationKugelrohr distillation of the resulting pale yellow oil (16.9 g)

Sources & evidence

ORD record
ord-25fa840ffdba46bc8e7c39429635feb2
Source dataset
uspto-grants-1997_06
Patent number
US05641883

Reaction notes

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