(+/-)-4-[1-(2,2-Dimethylpropyl-carbamoyl)-ethyl]-benzonitrile → (+/-)-4-[1-(2,2-Dimethylpropyl-carbamoyl)-ethyl]-benzylamine

HRID 1191048ノート

反応式

HRID 1191048 の反応式
[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][NH:4][C:5]([CH:7]([C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1)[CH3:8])=[O:6]>CO.Cl.[Pd]>[CH3:17][C:2]([CH3:1])([CH3:18])[CH2:3][NH:4][C:5]([CH:7]([C:9]1[CH:10]=[CH:11][C:12]([CH2:13][NH2:14])=[CH:15][CH:16]=1)[CH3:8])=[O:6]

参加物

5

反応物 1

HCID 58495675(+/-)-4-[1-(2,2-Dimethylpropyl-carbamoyl)-ethyl]-benzonitrile

生成物 1

HCID 58495650(+/-)-4-[1-(2,2-Dimethylpropyl-carbamoyl)-ethyl]-benzylamine収率 85%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid触媒HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

Bubble nitrogen into a solution of (±)-4-[1-(2,2-dimethylpropyl-carbamoyl)-ethyl]-benzonitrile (80 mg, 0.33 mmol) in methanol (9 mL) with 2 drops of concentrated HCl for 10 min. Add 10% Pd/C (Degussa type E101, 8 mg) and submit the mixture to hydrogenation at atmospheric pressure overnight. Filter the catalyst over Celite® and concentrate the filtrate in vacuo. Partition the solid between saturated aqueous NaHCO3 and EtOAc, and extract again with EtOAc. Dry the combined organics extracts over MgSO4, filter and concentrate in vacuo to afford the title compound as a yellow oil (69 mg, 85%). MS (ES+) m/z: 249 (M+H)+.

後処理

  1. customat atmospheric pressure overnight
  2. filtrationFilter the catalyst over Celite®
  3. concentrationconcentrate the filtrate in vacuo
  4. customPartition the solid between saturated aqueous NaHCO3 and EtOAc
  5. extractionextract again with EtOAc
  6. customDry the combined
  7. filtrationfilter
  8. concentrationconcentrate in vacuo

出典と根拠

ORDレコード
ord-b30a9b89adb144a785d56c86483119f4
出典データセット
uspto-grants-2014_03
特許番号
US08680091B2

反応ノート

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