Water → (8-Phenyl-1,4-dioxaspiro[4.5]decan-8-YL)methanamine

HRID 76927Notes

Reaction equation

HRID 76927 reaction equation
[C:1]1([C:7]2([C:17]#[N:18])[CH2:16][CH2:15][C:10]3([O:14][CH2:13][CH2:12][O:11]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[C:1]1([C:7]2([CH2:17][NH2:18])[CH2:8][CH2:9][C:10]3([O:14][CH2:13][CH2:12][O:11]3)[CH2:15][CH2:16]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 122302748-Phenyl-1,4-dioxaspiro[4.5]decane-8-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 20596179(8-Phenyl-1,4-dioxaspiro[4.5]decan-8-YL)methanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

A solution of the title compound of step 3 (10.0 g, 41.1 mmol) in dry THF (70 mL) was slowly added to a mixture of LiAlH4 (1.87 g, 49.3 mmol) in dry THF (25 mL) in a protective gas. The mixture was then stirred for 3 h with reflux. After the reaction mixture had cooled, a solution of water (1.87 mL, 104 mmol) diluted with a little THF was added in drops with ice cooling and subsequently stirred for 10 min. 15% aqueous NaOH (1.87 mL, 8.17 mmol) diluted with a little THF was then added in drops and water (5.6 mL) was then added again. The precipitate formed was filtered over diatomaceous earth and the solvent removed in a vacuum. The amine remained as residue.

Workup

  1. temperaturewith reflux
  2. temperatureAfter the reaction mixture had cooled
  3. additionwas added in drops with ice cooling
  4. stirringsubsequently stirred for 10 min
  5. additionwas then added again
  6. customThe precipitate formed
  7. filtrationwas filtered over diatomaceous earth
  8. customthe solvent removed in a vacuum

Sources & evidence

ORD record
ord-34a1b0a930bf49659305009da4faab7f
Source dataset
uspto-grants-2014_09
Patent number
US08835689B2

Reaction notes

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