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

HRID 1475626ノート

反応式

HRID 1475626 の反応式
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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

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 overnight under a hydrogen atmosphere at atmospheric pressure. 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 product obtained was triturated using a methanol/water mixture (70:30) and the solid was isolated. This gave 24.3 g (64.1% of theory) of the target compound.

後処理

  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. customThe product obtained
  5. customwas triturated
  6. customthe solid was isolated

出典と根拠

ORDレコード
ord-24c1b06f30f64039b0cd660d4c0fb54b
出典データセット
uspto-grants-2015_04
特許番号
US09018258B2

反応ノート

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