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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 922135Generated: November 1, 2026

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

https://huagongshe.com/reaction/922135

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantPotassium tert-butoxideHCID 23665647—
ReactantMethyl 1-{[(5-bromo-2-methylphenyl)acetyl]amino}-4-methoxy-4-(trifluoromethyl)cyclohexanecarboxylateHCID 71246345—
SolventDimethylformamideHCID 6228—
Product3-(5-Bromo-2-methylphenyl)-4-hydroxy-8-methoxy-8-(trifluoromethyl)-1-azaspiro[4.5]dec-3-en-2-oneHCID 90413776—

Reaction Conditions

Temperature80 °C

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09278925B2
Source datasetuspto-grants-2016_03
ORD IDord-a38e261f49974b209326d22340ff129e
Source noteuspto-grants-2016_03