1-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine → tert-Butyl 4-(2-oxoethyl)piperidine-1-carboxylate

HRID 988714Notes

Reaction equation

HRID 988714 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH:15]=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidineHCID 178418287HCID 178418287, compound

Product 1

HCID 10353694tert-Butyl 4-(2-oxoethyl)piperidine-1-carboxylateYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(tert-butoxycarbonyl)piperidine-4-ethanol (5.0 g, 22 mmol) in methylene chloride (100 mL) was treated with pyridinium chlorochromate (5.2 g, 24 mmol), and diatomaceous earth (5 g). After 3 days, the mixture was filtered through diatomaceous earth, concentrated, and the residue purified by column chromatography (SiO2: 20 to 30% EtOAc:hexanes) affording 4.0 g (81%) of the title compound.

Workup

  1. filtrationthe mixture was filtered through diatomaceous earth
  2. concentrationconcentrated
  3. customthe residue purified by column chromatography (SiO2: 20 to 30% EtOAc:hexanes)

Sources & evidence

ORD record
ord-d06f580173b3470fa3e53e81ead1ed46
Source dataset
uspto-grants-2003_10
Patent number
US06635657B1

Reaction notes

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