tert-Butyl 1-[3-(benzylamino)-4-chlorobenzyl]cyclopropanecarboxylate → tert-Butyl 1-(3-amino-4-chlorobenzyl)cyclopropanecarboxylate

HRID 626418노트

반응식

HRID 626418 반응식
C([NH:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:12][C:13]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14]1)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[NH2:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:12][C:13]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]1

참가 물질

4

반응물 1

HCID 68006927tert-Butyl 1-[3-(benzylamino)-4-chlorobenzyl]cyclopropanecarboxylate

생성물 1

HCID 67957815tert-Butyl 1-(3-amino-4-chlorobenzyl)cyclopropanecarboxylate

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

50.0 g (134.4 mmol) of tert-butyl 1-[3-(benzylamino)-4-chlorobenzyl]cyclopropanecarboxylate were dissolved in 1.5 liters of ethyl acetate, and 1.43 g (1.34 mmol) of palladium (10% on carbon) were added. The reaction mixture was stirred at RT under a hydrogen atmosphere at standard pressure overnight. The reaction mixture was then filtered off with suction through kieselguhr, and the filtrate was concentrated. The crude product was purified by chromatography on silica gel (mobile phase petroleum ether/ethyl acetate 10:1). The resulting product was stirred in a methanol/water mixture (70:30) and the solid was isolated. 24.3 g (64.1% of theory) of the target compound were obtained.

후처리

  1. filtrationThe reaction mixture was then filtered off with suction through kieselguhr
  2. concentrationthe filtrate was concentrated
  3. customThe crude product was purified by chromatography on silica gel (mobile phase petroleum ether/ethyl acetate 10:1)
  4. stirringThe resulting product was stirred in a methanol/water mixture (70:30)
  5. customthe solid was isolated
  6. custom24.3 g (64.1% of theory) of the target compound were obtained

출처 및 근거

ORD 기록
ord-490613a1bcb448629ee3d8bbccaa5500
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309198B2

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