Diethyl Ether → tert-Butyl 4-(2-oxoethyl)piperidine-1-carboxylate

HRID 1052218Notes

Reaction equation

HRID 1052218 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C([O-])(=O)C.[Na+].[OH:17][CH2:18][CH2:19][CH:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1.C(OCC)C>ClCCl>[O:17]=[CH:18][CH2:19][CH:20]1[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:25]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 517045Sodium AcetateHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidineHCID 178418287HCID 178418287, compound

Product 1

HCID 10353694tert-Butyl 4-(2-oxoethyl)piperidine-1-carboxylateYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of pyridinium chlorochromate (125.0 g) and sodium acetate (48.0 g) in dichloromethane (300 mL) was added a solution of tert-butyl 4-(2-hydroxyethyl)piperidine-1-carboxylate (89.0 g) in dichloromethane (150 mL) at 0° C. The reaction system was stirred at 25° C. for 3 hr, diethyl ether (300 mL) was added, and insoluble material was collected by filtration by silica gel column chromatography, and washed with diethyl ether (1000 mL) and dichloromethane/diethyl ether (1000 mL). The filtrate was concentrated to give the title compound (60.0 g).

Workup

  1. filtrationinsoluble material was collected by filtration by silica gel column chromatography
  2. washwashed with diethyl ether (1000 mL) and dichloromethane/diethyl ether (1000 mL)
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-5be801e9dc6d45acbb678b2426cb4aa0
Source dataset
uspto-grants-2016_07
Patent number
US09388195B2

Reaction notes

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