Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate → Benzyl 4-formylpiperidine-1-carboxylate

HRID 1634742Notes

Reaction equation

HRID 1634742 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][OH:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl.CCOCC>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH:17]=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 736490Benzyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 178418287HCID 178418287, compound

Product 1

HCID 2776272Benzyl 4-formylpiperidine-1-carboxylateYield 93%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

An ice cold solution of N-benzyloxycarbonyl-4-hydroxymethylpiperidine (2.5 g, 10 mmol) in 100 mL CH2Cl2 is treated with pyridinium chlorochromate (3.23 g, 15 mmol). The reaction is stirred at ambient temperature for 3 hours. The mixture was diluted with 100 mL Et2O and filtered through a plug of silica. The filtrate was concentrated in vacuo to provide 2.3 g of the title compound as a pale green liquid.

Workup

  1. filtrationfiltered through a plug of silica
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ad3b20eb3196434582f8384b52afc9f5
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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