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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 922133Generated: October 31, 2026

Hydrochloric Acid → 11-(5-Bromo-2-methylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-11-en-10-one

https://huagongshe.com/reaction/922133

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantPotassium tert-butoxideHCID 23665647—
ReactantMethyl 8-{[(5-bromo-2-methylphenyl)acetyl]amino}-1,4-dioxaspiro[4.5]decane-8-carboxylateHCID 67375909—
SolventDimethylformamideHCID 6228—
Product11-(5-Bromo-2-methylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-11-en-10-oneHCID 68271126—

Reaction Conditions

Temperature80 °C

Reaction Steps

1.92 g (17.08 mmol) of potassium tert-butoxide were added to 3.64 g (8.54 mmol) of methyl 8-{[(5-bromo-2-methylphenyl)acetyl]amino}-1,4-dioxaspiro[4.5]decane-8-carboxylate (Example 27A) in 43 ml of N,N-dimethylformamide. The reaction mixture was stirred at 80° C. for 30 minutes. For work-up, the cold reaction mixture was poured into 500 ml of ice-water and acidified to pH=4 with aqueous hydrochloric acid. The crude product was filtered off. Drying gave 2.49 g (74% of theory) of the title compound which was used without further characterization in the next step.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09278925B2
Source datasetuspto-grants-2016_03
ORD IDord-3013755f143d4aa9af5cf02df95828df
Source noteuspto-grants-2016_03