8-t-Butyl-3-cyano-1-oxaspiro(4,5)decane → 8-t-Butyl-3-aminomethyl-1-oxaspiro(4,5)decane

HRID 1684685Notes

Reaction equation

HRID 1684685 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([CH:11]1[CH2:22][CH2:21][C:14]2([O:18][CH2:17][CH:16]([C:19]#[N:20])[CH2:15]2)[CH2:13][CH2:12]1)([CH3:10])([CH3:9])[CH3:8]>C1COCC1>[C:7]([CH:11]1[CH2:22][CH2:21][C:14]2([O:18][CH2:17][CH:16]([CH2:19][NH2:20])[CH2:15]2)[CH2:13][CH2:12]1)([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 190401648-t-Butyl-3-cyano-1-oxaspiro(4,5)decaneHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 190401518-t-Butyl-3-aminomethyl-1-oxaspiro(4,5)decaneYield 65.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of lithium aluminum hydride (LAH) (2.19 g, 58 mmol) in THF (100 ml) was added 8-t-butyl-3-cyano-1-oxaspiro-(4,5)decane (8.5 g, 38.5 mmol) in THF (25 ml). The reaction mixture was refluxed for 3 hours. After cooling excess LAH was carefully destroyed by addition of saturated, aqueous sodium sulfate solution. The reaction mixture was filtrated from insoluble material and the filtrate was evaporated in vacuo. The pale yellow oil (8.6 g) was purified by Kugelrohr distillation (125°-135° C., 0.05 mbar) to yield the product as a colourless liquid (5.7 g, nD22 : 1.4817).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. customwas carefully destroyed by addition of saturated, aqueous sodium sulfate solution
  3. filtrationThe reaction mixture was filtrated from insoluble material
  4. customthe filtrate was evaporated in vacuo
  5. distillationThe pale yellow oil (8.6 g) was purified by Kugelrohr distillation (125°-135° C., 0.05 mbar)

Sources & evidence

ORD record
ord-25664153316f4040b27aa9d7af911cea
Source dataset
uspto-grants-1997_06
Patent number
US05641883

Reaction notes

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