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

HRID 1948591Notes

Reaction equation

HRID 1948591 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 mmole) was suspended in dry THF (4 ml) with the exclusion of atmospheric moisture. 8-isocyanato-8-phenyl-1,4-dioxaspiro[4.5]decane (2.29 g, 8.8 mmole, dissolved in 40 ml of dry THF) was then added dropwise within 20 minutes. After the end of the addition the reaction mixture was boiled under reflux for 4 hours. After cooling the reaction mixture, aqueous THF (1 ml H2O in 3 ml) was first of all carefully added, followed by 1.7 ml of 15% sodium hydroxide solution and finally 5 ml of H2O. The reaction mixture was stirred for 20 minutes and then filtered through diatomaceous earth. The solvent mixture obtained by washing the filter cake several times with ethyl acetate was concentrated by evaporation 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. additionAfter the end of the addition the reaction mixture
  2. temperatureunder reflux for 4 hours
  3. additionall carefully added
  4. filtrationfiltered through diatomaceous earth
  5. customThe solvent mixture obtained
  6. washby washing the filter cake several times with ethyl acetate
  7. concentrationwas concentrated by evaporation to dryness on a rotary evaporator

Sources & evidence

ORD record
ord-cadcc3530cbc4494ada6956d419cc7c4
Source dataset
uspto-grants-2013_03
Patent number
US08399503B2

Reaction notes

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