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

HRID 1191047노트

반응식

HRID 1191047 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-0350be10c0104e4fbe5b6b13766b71a5
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680091B2

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