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

HRID 1615739Notes

Reaction equation

HRID 1615739 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.[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

5

Reactant 2

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

Product 1

HCID 68760336(3S)-3-(cycloheptylmethyl)-6-(3,5-difluorophenyl)piperazin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Under a hydrogen atmosphere 0.590 g (1.29 mmol) methyl (S)-2-(benzyl-{2-(3,5-difluoro-phenyl)-2-[hydroxyimino]-ethyl}-amino)-3-cycloheptyl-propionate and 0.10 g palladium on charcoal (10%) in 10 ml of methanol were hydrogenated for 3 days at 50° C. and 3.45 bar hydrogen pressure. After elimination of the catalyst the filtrate was concentrated by rotary evaporation. The residue was stirred with petroleum ether and diisopropylether and filtered off.

Workup

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

Sources & evidence

ORD record
ord-076b948171e34560b1b7c8a7e4d27f1b
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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