HCID 54418173, compound → HCID 14541463, compound

HRID 345344Notes

Reaction equation

HRID 345344 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][CH:9]1[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[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][CH:9]1[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 54418173HCID 54418173, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 14541463HCID 14541463, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 11.8 g of ethyl 1-tert-butoxycarbonyl-4-(2-hydroxyethyl)-piperidine-2-carboxylate and 12.6 g of pyridinium chlorochromate in 175 ml methylene chloride is stirred under nitrogen at room temperature for 80 minutes. Mixture is filtered and purified by flash chromatography using ethyl acetate/hexane (25:75) to yield 1-(tert-butoxycarbonyl)-2-ethoxycarbonyl-piperidine-4-acetaldehyde.

Workup

  1. filtrationMixture is filtered
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-bb6394d7cc104ecaa4978ad65e61655d
Source dataset
uspto-grants-1991_10
Patent number
US05057506

Reaction notes

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