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 1615768ノート

反応式

HRID 1615768 の反応式
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

参加物

6

反応物 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、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-c5f5cf3a4e9f477a80283d4dcbac531a
出典データセット
uspto-grants-2014_07
特許番号
US08765763B2

反応ノート

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