Hydrochloric Acid → 3-(5-Bromo-2-methylphenyl)-4-hydroxy-8-methoxy-8-(trifluoromethyl)-1-azaspiro[4.5]dec-3-en-2-one

HRID 922135Notes

Reaction equation

HRID 922135 reaction equation
CC(C)([O-])C.[K+].[Br:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:34])=[C:12]([CH2:14][C:15]([NH:17][C:18]2([C:30]([O:32]C)=O)[CH2:23][CH2:22][C:21]([O:28][CH3:29])([C:24]([F:27])([F:26])[F:25])[CH2:20][CH2:19]2)=[O:16])[CH:13]=1.Cl>CN(C)C=O>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:34])=[C:12]([C:14]2[C:15](=[O:16])[NH:17][C:18]3([CH2:19][CH2:20][C:21]([O:28][CH3:29])([C:24]([F:26])([F:25])[F:27])[CH2:22][CH2:23]3)[C:30]=2[OH:32])[CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 71246345Methyl 1-{[(5-bromo-2-methylphenyl)acetyl]amino}-4-methoxy-4-(trifluoromethyl)cyclohexanecarboxylate

Product 1

HCID 904137763-(5-Bromo-2-methylphenyl)-4-hydroxy-8-methoxy-8-(trifluoromethyl)-1-azaspiro[4.5]dec-3-en-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2.26 g (20.16 mmol) of potassium tert-butoxide were added to 4.70 g (10.08 mmol) of methyl 1-{[(5-bromo-2-methylphenyl)acetyl]amino}-4-methoxy-4-(trifluoromethyl)cyclohexanecarboxylate (Example 36A) in 50 ml of N,N-dimethylformamide. The reaction mixture was stirred at 80° C. for 60 minutes. For work-up, the cold reaction mixture was poured into 800 ml of ice-water and acidified with aqueous hydrochloric acid. The crude product was filtered off and dried. This gave 3.68 g (84% of theory) of the title compound as a beige powder.

Workup

  1. customFor work-up, the cold reaction mixture
  2. filtrationThe crude product was filtered off
  3. customdried

Sources & evidence

ORD record
ord-a38e261f49974b209326d22340ff129e
Source dataset
uspto-grants-2016_03
Patent number
US09278925B2

Reaction notes

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