Sodium Thiosulfate → 1-(3-Methoxy-4-nitrophenyl)piperidin-4-one
Reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([N:34]2[CH2:39][CH2:38][CH:37]([OH:40])[CH2:36][CH2:35]2)[CH:28]=[CH:29][C:30]=1[N+:31]([O-:33])=[O:32].[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:23][O:24][C:25]1[CH:26]=[C:27]([N:34]2[CH2:39][CH2:38][C:37](=[O:40])[CH2:36][CH2:35]2)[CH:28]=[CH:29][C:30]=1[N+:31]([O-:33])=[O:32]Participants
6
Procedure
Dess-Martin periodinane (13.62 g, 32.11 mmol) was added to 1-(3-methoxy-4-nitrophenyl)piperidin-4-ol (INTERMEDIATE 17, 5.4 g, 21.41 mmol) in DCM (120 mL) at 0° C. and the reaction mixture was stirred for 30 min. The reaction mixture was then allowed to warm to RT and stirred for an additional 4 h. The reaction solution was poured into a mixture of 20% aqueous Na2S2O3 (50 mL) and saturated aqueous NaHCO3 (50 mL) and the biphasic mixture was stirred at RT for 1 h. The mixture was partitioned and organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by chromatography on silica gel (5% MeOH/DCM) to give the title product (4.28 g, 80%). m/z 251.
Workup
- stirringstirred for an additional 4 h
- stirringthe biphasic mixture was stirred at RT for 1 h
- customThe mixture was partitioned
- washorganic layer was washed with brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude residue was purified by chromatography on silica gel (5% MeOH/DCM)
Sources & evidence
- ORD record
- ord-dd5de8c61a994fa18853c4e6085c527f
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08461170B2
Reaction notes
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