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

HRID 232549Notes

Reaction equation

HRID 232549 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-f5529c879f304284884bcc862b4acc74
Source dataset
uspto-grants-1997_01
Patent number
US05591741

Reaction notes

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