Diethyl (2-cyanoethyl)(3,4-difluorophenyl)propanedioate → Ethyl 3-(3,4-difluorophenyl)-2-oxopiperidine-3-carboxylate

HRID 71110

Reaction equation

HRID 71110 reaction equation
[C:1]([CH2:3][CH2:4][C:5]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[CH:17]=1)([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6](OCC)=[O:7])#[N:2]>[Co].N>[F:23][C:18]1[CH:17]=[C:16]([C:5]2([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4][CH2:3][CH2:1][NH:2][C:6]2=[O:7])[CH:21]=[CH:20][C:19]=1[F:22]

Participants

4

Reactant 1

HCID 66608241Diethyl (2-cyanoethyl)(3,4-difluorophenyl)propanedioate

Product 1

HCID 66607999Ethyl 3-(3,4-difluorophenyl)-2-oxopiperidine-3-carboxylateYield 79.3%

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 222AmmoniaSolvent

Procedure

A mixture of diethyl (2-cyanoethyl)(3,4-difluorophenyl)propanedioate (15.2 g), Raney cobalt (75 g) and ammonia (2M ethanol solution, 150 mL) was stirred at room temperature for 3 days under a hydrogen atmosphere. The insoluble material was filtered off through celite, and the filtrate was concentrated under reduced pressure. The residue was washed with diisopropylether to give the title compound (10.5 g).

Workup

  1. filtrationThe insoluble material was filtered off through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washThe residue was washed with diisopropylether

Sources & evidence

ORD record
ord-42390afab45e45948b53e8b96a946d2e
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Linked notes

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