Hydrochloric Acid → 3-(5-Bromo-2-methylphenyl)-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-one

HRID 1466455Notes

Reaction equation

HRID 1466455 reaction equation
CC(C)([O-])C.[K+].[Br:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:28])=[C:12]([CH2:14][C:15]([NH:17][C:18]2([C:24]([O:26]C)=O)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:16])[CH:13]=1.O.Cl>CN(C)C=O>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:28])=[C:12]([C:14]2[C:15](=[O:16])[NH:17][C:18]3([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]3)[C:24]=2[OH:26])[CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 23665647Potassium tert-butoxideHCID 67375467Methyl 1-{[(5-bromo-2-methylphenyl)acetyl]amino}cyclohexanecarboxylate

Product 1

HCID 673745843-(5-Bromo-2-methylphenyl)-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

1.71 g (15.2 mmol) of potassium tert-butoxide were added to 2.80 g (7.60 mmol) of the compound from Example 12A in 15 ml of N,N-dimethylformamide. The reaction mixture was heated at 80° C. for 15 minutes. After cooling, water was added and aqueous hydrogen chloride solution was added dropwise. The precipitate was filtered off with suction, washed with water and dried. This gave 2.33 g (90% of theory) of the title compound.

Workup

  1. temperatureAfter cooling
  2. filtrationThe precipitate was filtered off with suction
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-47d3e58d724c4246812cbcfb3c90848c
Source dataset
uspto-grants-2015_04
Patent number
US09000026B2

Reaction notes

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