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tert-Butyl 1-[(4-chloro-3-nitrophenyl)(hydroxy)methyl]cyclopropanecarboxylate → tert-Butyl 1-[(3-amino-4-chlorophenyl)(hydroxy)methyl]cyclopropanecarboxylate

HRID 1475678
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HRID 1475678 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:19])[C:9]2([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:11][CH2:10]2)=[CH:4][C:3]=1[N+:20]([O-])=O.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:20][C:3]1[CH:4]=[C:5]([CH:8]([OH:19])[C:9]2([C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[CH2:10][CH2:11]2)[CH:6]=[CH:7][C:2]=1[Cl:1]
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참가 물질

5

반응물 2

HCID 67958223tert-Butyl 1-[(4-chloro-3-nitrophenyl)(hydroxy)methyl]cyclopropanecarboxylateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 67957785tert-Butyl 1-[(3-amino-4-chlorophenyl)(hydroxy)methyl]cyclopropanecarboxylate

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

2.72 g (8.30 mmol) of tert-butyl 1-[(4-chloro-3-nitrophenyl)(hydroxy)methyl]cyclopropane-carboxylate were dissolved in 100 ml of ethyl acetate, and 177 mg of palladium on carbon (10%) were added. For three days, the reaction mixture was stirred vigorously under a stationary atmosphere of hydrogen at atmospheric pressure. The mixture was then filtered through Celite and the filtrate obtained was evaporated to dryness. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1). This gave 1.97 g of the target compound (80% of theory).

후처리

  1. filtrationThe mixture was then filtered through Celite
  2. customthe filtrate obtained
  3. customwas evaporated to dryness
  4. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1)

출처 및 근거

ORD 기록
ord-995c9272c1e84bc7bea44c1951a2c89f
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09018258B2

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