Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate → tert-Butyl 4-formylpiperidine-1-carboxylate

HRID 871071Notes

Reaction equation

HRID 871071 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.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[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

HCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 178418287HCID 178418287, compound

Product 1

HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 1B (5 g, 23.22 mmol) in dichloromethane (50 mL) was added pyridinium chlorochromate (10.01 g, 46.4 mmol) and the mixture stirred for 12 hours. The mixture was filtered through diatomaceous earth with dichloromethane, concentrated and purified by column chromatography on silica gel (Isco®, Redi-Sep® column), eluting with 40% ethyl acetate in hexane to afford the title compound. LCMS: 213.9 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth with dichloromethane
  2. concentrationconcentrated
  3. custompurified by column chromatography on silica gel (Isco®, Redi-Sep® column)
  4. washeluting with 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-a531ad0c9ad14246a2f82d310475d7e1
Source dataset
uspto-grants-2015_03
Patent number
US08969375B2

Reaction notes

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