methyl (S)-2-(benzyl-{2-(3,5-difluoro-phenyl)-2-[hydroxyimino]-ethyl}-amino)-3-cycloheptyl-propionate → (3R)-3-(cycloheptylmethyl)-6-(3,5-difluorophenyl)piperazin-2-one

HRID 1615768Notes

Reaction equation

HRID 1615768 reaction equation
C([N:8]([CH2:22][C:23]([C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[C:28]([F:33])[CH:27]=1)=[N:24]O)[C@H:9]([CH2:14][CH:15]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:10](OC)=[O:11])C1C=CC=CC=1.C(N(CC(C1C=C(F)C=C(F)C=1)=NO)[C@@H](CC1CCCCCC1)C(OC)=O)C1C=CC=CC=1.[H][H]>[Pd].CO>[CH:15]1([CH2:14][C@H:9]2[NH:8][CH2:22][CH:23]([C:26]3[CH:31]=[C:30]([F:32])[CH:29]=[C:28]([F:33])[CH:27]=3)[NH:24][C:10]2=[O:11])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 86668536methyl (S)-2-(benzyl-{2-(3,5-difluoro-phenyl)-2-[hydroxyimino]-ethyl}-amino)-3-cycloheptyl-propionateHCID 86668541methyl (R)-2-(benzyl-{2-(3,5-difluoro-phenyl)-2-[hydroxyimino]-ethyl}-amino)-3-cycloheptyl-propionateHCID 178418361HCID 178418361, compound

Product 1

HCID 68760174(3R)-3-(cycloheptylmethyl)-6-(3,5-difluorophenyl)piperazin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Under a hydrogen atmosphere 5.5 g (12.0 mmol) methyl (R)-2-(benzyl-{2-(3,5-difluoro-phenyl)-2-[hydroxyimino]-ethyl}-amino)-3-cycloheptyl-propionate (this compound may be prepared analogously to the synthesis of methyl (S)-2-(benzyl-{2-(3,5-difluoro-phenyl)-2-[hydroxyimino]-ethyl}-amino)-3-cycloheptyl-propionate described herein using the corresponding (R)-configured starting component) and 0.70 g palladium on charcoal (10%) were hydrogenated in 30 ml of methanol for 3 days at 50° C. to 60° C. and 3 bar hydrogen pressure. After elimination of the catalyst the filtrate was concentrated by rotary evaporation. Purification was carried out by flash chromatography.

Workup

  1. concentrationAfter elimination of the catalyst the filtrate was concentrated by rotary evaporation
  2. customPurification

Sources & evidence

ORD record
ord-c5f5cf3a4e9f477a80283d4dcbac531a
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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