Ammonium formate → HCID 22380663, compound

HRID 895647Notes

Reaction equation

C(O[CH:5]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[O:21][CH2:22][C:23]([CH3:26])([CH3:25])[N:24]=2)=[CH:16][CH:15]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH3:13])(=O)C.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:25][C:23]1([CH3:26])[CH2:22][O:21][C:20]([C:17]2[CH:18]=[CH:19][C:14]([CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[O:12][CH3:13])=[CH:15][CH:16]=2)=[N:24]1

Participants

Conditions

Temperature: 60 °C

Procedure

In an amount of 23.5 mg of the 1-[4-(4,4-dimethyloxazolin-2-yl)phenyl]-1-(2-methoxyphenyl)methyl acetate obtained above was dissolved in methanol (0.47 ml), added with 10% palladium/carbon (24 mg) and ammonium formate (42 mg) under argon atmosphere and stirred at 60° C. for 2 hours. After insoluble matters were removed by filtration, the solvent was evaporated under reduced pressure. The residue was purified by preparative thin layer silica gel column chromatography (developing solvent: hexane:ethyl acetate=1:1) to obtain 14.4 mg of the title compound. Yield: 73%.

Workup

customAfter insoluble matters were removed by filtration
customthe solvent was evaporated under reduced pressure
customThe residue was purified by preparative thin layer silica gel column chromatography (developing solvent: hexane:ethyl acetate=1:1)

Sources & evidence

ORD record: ord-4576680ac5d542658cb4b108f8e82f1f
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06916822B2

Reaction notes

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