Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate → tert-Butyl 4-formylpiperidine-1-carboxylate
Reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[CH:2]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)=[O:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To the solution of tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (139.5 mmol) in DCM (300 ml) was added PCC (209.3 mmol, 1.5 eq) at 0° C. The reaction mixture was then allowed to stir at 25° C. for 16 h. The mixture was filtered through celite, washed with DCM (2×200 ml), and the organics were concentrated and purified by silica gel column chromatography (10% EtOAc in DCM) to obtain the desired compound. Yield: 42%
Workup
- filtrationThe mixture was filtered through celite
- washwashed with DCM (2×200 ml)
- concentrationthe organics were concentrated
- custompurified by silica gel column chromatography (10% EtOAc in DCM)
Sources & evidence
- ORD record
- ord-4da336aad218483ba654315cc3232d57
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08278319B2
Reaction notes
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