1'-Benzyl-5-fluoro-3H-spiro[2-benzofuran-1,4'-piperidin]-3-one → 5-Fluoro-3h-spiro[isobenzofuran-1,4'-piperidin]-3-one
Reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2([C:17]3[CH:18]=[CH:19][C:20]([F:22])=[CH:21][C:16]=3[C:15](=[O:23])[O:14]2)[CH2:10][CH2:9]1)C1C=CC=CC=1>C(O)C.Cl.[Pd]>[F:22][C:20]1[CH:19]=[CH:18][C:17]2[C:11]3([O:14][C:15](=[O:23])[C:16]=2[CH:21]=1)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3Participants
Procedure
1′-Benzyl-5-fluoro-3H-spiro[2-benzofuran-1,4′-piperidin]-3-one (0.622 g, 2 mmol) was suspended in ethanol (6 ml). The mixture was acidified with a few drops of HCl 37%. Pd/C 10% (65 mg, 0.06 mmol) was added. The mixture was refluxed under an hydrogen atmosphere for 1 hour then cooled to room temperature, purged with argon and diluted with dichloromethane. The catalyst was filtered and the filtrate was concentrated in vacuo. The white solid was dissolved in water (20 ml). The solution was basified with a 2M Na2CO3 solution and extracted 3 times with dichloromethane. The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo to yield 0.42 g (96%) 5-fluoro-3H-spiro[2-benzofuran-1,4′-piperidin]-3-one as a white solid. MS m/e: 222 (M+H+).
Workup
- temperatureThe mixture was refluxed under an hydrogen atmosphere for 1 hour
- custompurged with argon
- additiondiluted with dichloromethane
- filtrationThe catalyst was filtered
- concentrationthe filtrate was concentrated in vacuo
- dissolutionThe white solid was dissolved in water (20 ml)
- extractionextracted 3 times with dichloromethane
- dry with materialThe combined extracts were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-b6f2c5ed79144005b3426569bab4d3b0
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08664216B2
Reaction notes
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