Ethanol → HCID 18442718, compound

HRID 2273020Notes

Reaction equation

HRID 2273020 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C:10](=O)[CH2:9]1)=O)(C)(C)C.[C-]#N.[K+].[C:17](=[O:20])([O-])[O-].[NH4+:21].[NH4+:22].[CH2:23]([OH:25])C>O>[CH2:11]1[C:10]2([NH:22][C:23](=[O:25])[NH:21][C:17]2=[O:20])[CH2:9][NH:8][CH2:12]1

Participants

6

Reactant 4

HCID 702EthanolHCID 9032Potassium CyanideHCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 517111Ammonium Carbonate

Product 1

HCID 18442718HCID 18442718, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

3-Oxo-pyrrolidine-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 2 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-a9999800bf7e470996918b440e05c1d7
Source dataset
uspto-grants-2015_09
Patent number
US09120804B2

Reaction notes

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