Ethanol → (S)-7-(4-bromo-phenyl)-1,3-diaza-spiro[4.4]nonane-2,4-dione

HRID 2421501Notes

Reaction equation

HRID 2421501 reaction equation
[C:1](=[O:4])([O-])[O-].[NH4+:5].[NH4+:6].[C-]#N.[K+].O.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C@H:18]2[CH2:22][CH2:21][C:20](=O)[CH2:19]2)=[CH:14][CH:13]=1.[CH2:24]([OH:26])C>>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[CH2:22][CH2:21][C@:20]3([NH:6][C:24](=[O:26])[NH:5][C:1]3=[O:4])[CH2:19]2)=[CH:14][CH:13]=1

Participants

6

Reactant 5

HCID 702EthanolHCID 962WaterHCID 9032Potassium CyanideHCID 517111Ammonium CarbonateHCID 25002103(S)-3-(4-Bromophenyl)cyclopentan-1-one

Product 1

HCID 67259304(S)-7-(4-bromo-phenyl)-1,3-diaza-spiro[4.4]nonane-2,4-dioneYield 95%

Conditions

Temperature
80 °C

Procedure

To a round bottom flask charged with ammonium carbonate (268 g, 2.79 mol) and potassium cyanide (44.4 g, 0.681 mol) was added water (1500 mL, 82 mol). The mixture was heated at 80° C. and a solution of (S)-3-(4-bromo-phenyl)-cyclopentanone (148.09 g, 0.62 mol) in ethanol (1500 mL, 25 mol) was added. The reaction mixture was heated to reflux overnight. The reaction mixture was cooled to room temperature. The crude reaction mixture was filtered and washed with water. The solid was triturated with ether (1.5 L), filtered, washed with ether and dried under vacuum to yield (S)-7-(4-bromo-phenyl)-1,3-diaza-spiro[4.4]nonane-2,4-dione (181.29 g, 95%) as a 1:1 mixture of diastereomers.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customThe crude reaction mixture
  5. filtrationwas filtered
  6. washwashed with water
  7. customThe solid was triturated with ether (1.5 L)
  8. filtrationfiltered
  9. washwashed with ether
  10. customdried under vacuum

Sources & evidence

ORD record
ord-e9da1faca28c46adbe8a8e0788001628
Source dataset
uspto-grants-2011_06
Patent number
US07956195B2

Reaction notes

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