Water → 1-Oxa-4-azaspiro[4.5]decane-3,3-dimethanol

HRID 1703747Notes

Reaction equation

HRID 1703747 reaction equation
[OH:1][CH2:2][C:3]([CH2:7][OH:8])([CH2:5][OH:6])[NH2:4].[C:9]1(=O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.O>C1(C)C=CC=CC=1>[CH2:2]([C:3]1([CH2:7][OH:8])[NH:4][C:9]2([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[O:6][CH2:5]1)[OH:1]

Participants

5

Reactant 3

HCID 962WaterHCID 6503Tris(hydroxymethyl)aminomethaneHCID 7967Cyclohexanone

Product 1

HCID 3251041-Oxa-4-azaspiro[4.5]decane-3,3-dimethanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Tris-(hydroxymethyl)-aminomethane (24.23 grams; 0.2 mole) and cyclohexanone (19.63 grams; 0.2 mole) were refluxed overnight in 150 mls of toluene, using a water separator to remove approximately 3.6 mls of water. The toluene was then removed by distillation and the residue was recrystallized from acetone to obtain 32 grams (79.5% of theoretical; m.p. 117°-119° C.) of the desired compound.

Workup

  1. customto remove approximately 3.6 mls of water
  2. customThe toluene was then removed by distillation
  3. customthe residue was recrystallized from acetone

Sources & evidence

ORD record
ord-71476f08ce7e4592912d35338c49f52f
Source dataset
uspto-grants-1978_11
Patent number
US04125518

Reaction notes

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