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

HRID 1191047ノート

反応式

HRID 1191047 の反応式
C[Al](C)C.[CH3:5][C:6]([CH3:10])([CH3:9])[CH2:7][NH2:8].[C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH3:25])[C:20](OCC)=[O:21])=[CH:15][CH:14]=1)#[N:12]>C(Cl)Cl>[CH3:5][C:6]([CH3:10])([CH3:9])[CH2:7][NH:8][C:20]([CH:19]([C:16]1[CH:15]=[CH:14][C:13]([C:11]#[N:12])=[CH:18][CH:17]=1)[CH3:25])=[O:21]

参加物

5

反応物 3

HCID 79882NeopentylamineHCID 4550989Ethyl 2-(4-cyanophenyl)propanoateHCID 16682925Trimethylaluminum

生成物 1

HCID 58495675(+/-)-4-[1-(2,2-Dimethylpropyl-carbamoyl)-ethyl]-benzonitrile収率 41%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Add AlMe3 (1.72 mL, 3.44 mmol, 2M solution in hexane) to a solution of 2,2-dimethyl-propylamine (402 μL, 3.44 mmol) in DCM (0.5 mL) under nitrogen atmosphere. Stir the mixture for 15 min at room temperature and add ethyl 2-(4-cyanophenyl)propanoate. Heat the mixture at 40° C. overnight. Quench the reaction with 10N aqueous HCl and extract twice with DCM. Dry the combined organics extracts over Na2SO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (7:3) to obtain the desired intermediate (170 mg, 41%).

後処理

  1. temperatureHeat the mixture at 40° C. overnight
  2. customQuench
  3. customthe reaction with 10N aqueous HCl
  4. extractionextract twice with DCM
  5. customDry the combined
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurify by chromatography on silica gel eluting with hexane/EtOAc (7:3)

出典と根拠

ORDレコード
ord-0350be10c0104e4fbe5b6b13766b71a5
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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