Isopropanol → Benzyl 4-oxopiperidine-1-carboxylate

HRID 1584374Notes

Reaction equation

HRID 1584374 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C(O)(C)C>C(Cl)Cl>[O:1]=[C:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 2794620Benzyl 4-Hydroxy-1-piperidinecarboxylateHCID 178418287HCID 178418287, compound

Product 1

HCID 643496Benzyl 4-oxopiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Celite (66 g) was added to a solution of 4-hydroxy-N-CBZ-piperidine (18 g, 76.5 mmol) in methylene chloride (500 ml), followed by pyridinium chlorochromate (33 g, 153 mmol). The mixture was stirred overnight, and then isopropyl alcohol (12 ml) was added over a period of 3 hours. The reaction mixture was filtered through silica gel and the filter cake was repeatedly rinsed with methylene chloride and ethyl acetate. The combined filtrates were evaporated under reduced pressure. Silica gel chromatography using 50% ethyl acetate/hexane, gave 4-oxo-N-CBZ-piperidine as a yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered through silica gel
  2. washthe filter cake was repeatedly rinsed with methylene chloride and ethyl acetate
  3. customThe combined filtrates were evaporated under reduced pressure

Sources & evidence

ORD record
ord-745131541dae498f9006804bca08c8b0
Source dataset
uspto-grants-1999_08
Patent number
US05932595

Reaction notes

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