Ethanol → 8-Methoxy-8-(methoxymethyl)-1,3-diazaspiro[4.5]decane-2,4-dione

HRID 922123Notes

Reaction equation

HRID 922123 reaction equation
[C:1](=[O:4])([O-])[O-].[NH4+:5].[NH4+:6].[C-]#N.[Na+].[CH3:10][O:11][C:12]1([CH2:19][O:20][CH3:21])[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1.[CH2:22]([OH:24])C>O>[CH3:10][O:11][C:12]1([CH2:19][O:20][CH3:21])[CH2:17][CH2:16][C:15]2([NH:6][C:22](=[O:24])[NH:5][C:1]2=[O:4])[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 702EthanolHCID 8929Sodium CyanideHCID 517111Ammonium CarbonateHCID 857431314-Methoxy-4-(methoxymethyl)cyclohexanone

Product 1

HCID 712462848-Methoxy-8-(methoxymethyl)-1,3-diazaspiro[4.5]decane-2,4-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

5.74 g (59.7 mmol) of ammonium carbonate and 1.46 g (29.8 mmol) of sodium cyanide were dissolved in 33 ml of water. 2.57 g (14.9 mmol) of a solution of the compound from Example 12A in 33 ml of ethanol were added dropwise at room temperature and the mixture was stirred at 60° C. overnight. The reaction mixture was concentrated to a quarter of its original volume and extracted repeatedly with dichloromethane and ethyl acetate, and the organic phases were dried over sodium sulphate, filtered and concentrated. This gave 675 mg (19% of theory) of the title compound as a diastereomer mixture which was reacted without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated to a quarter of its original volume
  2. extractionextracted repeatedly with dichloromethane and ethyl acetate
  3. dry with materialthe organic phases were dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThis gave 675 mg (19% of theory) of the title compound as a diastereomer mixture which was reacted without further purification

Sources & evidence

ORD record
ord-80270b3e310c4d45b6463f212a65ab41
Source dataset
uspto-grants-2016_03
Patent number
US09278925B2

Reaction notes

Loading…