Water → Methyl-(8-phenyl-1,4-dioxaspiro[4.5]dec-8-yl)amine

HRID 1095494Notes

Reaction equation

HRID 1095494 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]([C:10]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:19][CH2:18][C:13]2([O:17][CH2:16][CH2:15][O:14]2)[CH2:12][CH2:11]1)=[C:8]=O.[OH-].[Na+].O>C1COCC1>[CH3:8][NH:7][C:10]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:11][CH2:12][C:13]2([O:17][CH2:16][CH2:15][O:14]2)[CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 125955658-Isocyanato-8-phenyl-1,4-dioxaspiro[4.5]decaneHCID 21226445Aluminium lithium hydride

Product 1

HCID 12595582Methyl-(8-phenyl-1,4-dioxaspiro[4.5]dec-8-yl)amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

LiAlH4 (535 mg, 14.08 mmol) was suspended in dry THF (4 ml) with exclusion of moisture from the atmosphere. 8-Isocyanato-8-phenyl-1,4-dioxaspiro[4.5]decane (2.29 g, 8.8 mmol, dissolved in 40 ml of dry THF) was added dropwise in the course of 20 min. When the addition was complete, the reaction mixture was heated to the boiling point under reflux for 4 h. After cooling, first aqueous THF (1 ml of H2O in 3 ml) was cautiously added to the reaction mixture, while cooling with ice, then 1.7 ml of 15 per cent strength sodium hydroxide solution and finally 5 ml of H2O. The mixture was stirred for 20 min and then filtered over silica gel. The solvent mixture obtained after washing the filter cake with ethyl acetate several times was concentrated to dryness on a rotary evaporator. The desired product was obtained in a yield of 2.1 g (97%) as a viscous oil.

Workup

  1. additionWhen the addition
  2. temperaturethe reaction mixture was heated to the boiling point
  3. temperatureunder reflux for 4 h
  4. temperatureAfter cooling
  5. temperaturewhile cooling with ice
  6. filtrationfiltered over silica gel
  7. customThe solvent mixture obtained
  8. washafter washing the filter cake with ethyl acetate several times
  9. concentrationwas concentrated to dryness on a rotary evaporator

Sources & evidence

ORD record
ord-74dd9a04b79446bd872a63c28d90691d
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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