1-Boc-3-hydroxypiperidine → Tert-butyl 3-oxopiperidine-1-carboxylate

HRID 1639994Notes

Reaction equation

HRID 1639994 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[OH:12][CH:13]1[CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]1>C(Cl)Cl.C(OCC)C>[O:12]=[C:13]1[CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]1

Participants

5

Reactant 2

HCID 5456991-Boc-3-hydroxypiperidineHCID 178418287HCID 178418287, compound

Product 1

HCID 2756825Tert-butyl 3-oxopiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of pyridinium chlorochromate (3.21 g, 0.0149 mol) in methylene chloride (18 mL) was added another solution of tert-butyl 3-hydroxypiperidine-1-carboxylate (1.00 g, 0.00497 mol) in 7 mL methylene chloride at rt. After stirring for 18 h, the reaction mixture was diluted with diethyl ether, filtered through a bed of celite, concentrated in-vacuo, and then purified by Combiflash to afford the desired product verified by NMR.

Workup

  1. filtrationfiltered through a bed of celite,
  2. concentrationconcentrated in-vacuo
  3. custompurified by Combiflash

Sources & evidence

ORD record
ord-2718b728d451434c96292d792fdeddca
Source dataset
uspto-grants-2012_02
Patent number
US08110581B2

Reaction notes

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