Ethanol → 2,5,7-Triazaspiro[3.4]octane-6,8-dione

HRID 2273021Notes

Reaction equation

HRID 2273021 reaction equation
C(OC([N:8]1[CH2:11][C:10](=O)[CH2:9]1)=O)(C)(C)C.[C-]#N.[K+].[C:16](=[O:19])([O-])[O-].[NH4+:20].[NH4+:21].[CH2:22]([OH:24])C>O>[CH2:11]1[C:10]2([NH:21][C:22](=[O:24])[NH:20][C:16]2=[O:19])[CH2:9][NH:8]1

Participants

6

Reactant 4

HCID 702EthanolHCID 9032Potassium CyanideHCID 517111Ammonium CarbonateHCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 666007202,5,7-Triazaspiro[3.4]octane-6,8-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

3-Oxo-azetidine-1-carboxylic acid tert-butyl ester (1 eq.) and potassium cyanide (1.3 eq) are dissolved in ethanol before ammonium carbonate (8 eq.) in water is added. The mixture is heated to 90° C. for 19 h and monitored by LCMS. Upon completion, the solvent is removed in vacuum. The residue is diluted with water and the product filtered off. Boc-deprotection under standard conditions gives the desired hydantoine as HCl-salt ready for further modifications.

Workup

  1. additionis added
  2. customUpon completion, the solvent is removed in vacuum
  3. additionThe residue is diluted with water
  4. filtrationthe product filtered off

Sources & evidence

ORD record
ord-350c788c2115403eb7d378c904a62964
Source dataset
uspto-grants-2015_09
Patent number
US09120804B2

Reaction notes

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