Cyclohexane ethylacetate → Tert-butyl 3-(3-amino-4-chlorophenyl)propanoate

HRID 1476056노트

반응식

HRID 1476056 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:4][C:3]=1[N+:17]([O-])=O.C1CCCCC1.C(OCC)(=O)C>[Pd].C(O)C.C1COCC1>[C:13]([O:12][C:10](=[O:11])[CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([NH2:17])[CH:4]=1)([CH3:16])([CH3:14])[CH3:15]

참가 물질

6

반응물 2

HCID 21867204Cyclohexane ethylacetateHCID 58136394tert-Butyl (2E)-3-(4-chloro-3-nitrophenyl)prop-2-enoate

생성물 1

HCID 58136497Tert-butyl 3-(3-amino-4-chlorophenyl)propanoate

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

At room temperature, 500 mg of palladium on carbon (10%) were added to a solution of 6.74 g (23.76 mmol) of tert-butyl (2E)-3-(4-chloro-3-nitrophenyl)prop-2-enoate in 200 ml of ethanol and 20 ml of THF, and the mixture was hydrogenated under atmospheric pressure for 12 h. After the reaction had gone to completion (monitored by TLC; mobile phase cyclohexane/ethyl acetate 1:1), the reaction solution was filtered through kieselguhr and the filtrate was concentrated under reduced pressure. The crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 4:1→2:1). This gave 1.40 g (5.47 mmol, 23% of theory) of the title compound.

후처리

  1. filtrationthe reaction solution was filtered through kieselguhr
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 4:1→2:1)

출처 및 근거

ORD 기록
ord-867ead1e79c645648e6e96864b8f5a93
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018414B2

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