Triacetoxyperiodinane → Tert-butyl 3-oxopiperidine-1-carboxylate
Reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of tert-butyl 3-hydroxypiperidine-1-carboxylate (5 g, 24.84 mmol, 1.0 equiv) in DCM (125 mL) was added Dess-Martin periodinane (11.59 g, 27.33 mmol, 1.1 equiv) at 0° C. in a few portions. The solution was stirred at 0° C. for a while and allowed to warm to room temperature slowly. The solution was stirred at room temperature for 18 hrs. A lot of white solid suspended. The white solid was removed by filtration, eluted with EtOAc (100 mL). The combined organic phase was washed with saturated solution of NaHCO3 (50 mL), dried over anhydrous Na2SO4, concentrated to afford 4.28 g (yield 86%) of tert-butyl 3-oxopiperidine-1-carboxylate as a white solid.
Workup
- temperatureto warm to room temperature slowly
- stirringThe solution was stirred at room temperature for 18 hrs
- customThe white solid was removed by filtration
- washeluted with EtOAc (100 mL)
- washThe combined organic phase was washed with saturated solution of NaHCO3 (50 mL)
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-54ffa56145d248739de291c3b3d5714c
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09226923B2
Reaction notes
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