Ethyl 3-(4-nitrobenzyl)cyclobutanecarboxylate → Ethyl 3-(4-aminobenzyl)cyclobutanecarboxylate

HRID 1713858노트

반응식

HRID 1713858 반응식
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]([CH2:8][CH:9]2[CH2:12][CH:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:10]2)=[CH:6][CH:5]=1)([O-])=O>CCOC(C)=O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH:9]2[CH2:10][CH:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:12]2)=[CH:18][CH:19]=1

참가 물질

3

반응물 1

HCID 59464076Ethyl 3-(4-nitrobenzyl)cyclobutanecarboxylate

생성물 1

HCID 59464168Ethyl 3-(4-aminobenzyl)cyclobutanecarboxylate수율 50%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Ethyl 3-(4-nitrobenzyl)cyclobutanecarboxylate (4.02 mmol) was stirred in EtOAc (20 mL) at room temperature and nitrogen was bubbled through. 10% Palladium on carbon (160 mg) was added and the reaction vessel was put under an atmosphere of hydrogen. The mixture was stirred overnight then filtered through diatomaceous earth and concentrated by evaporation under reduced pressure. The residue was purified by chromatography eluting with 0-55% EtOAc/isohexane to give the title compound (466 mg, 50%) as an oil; 1H NMR δ 1.15-1.20 (3H, m), 1.77-1.94 (2H, m), 2.13-2.20 (2H, m), 2.33-2.37 (2H, m), 2.43-2.46 (1H, m), 2.53-2.56 (1H, m), 2.92-3.07 (1H, m), 4.01-4.08 (2H, m), 4.77 (2H, d), 6.46-6.49 (2H, m), 6.78-6.82 (2H, m); MS m/e M+MeCN 275.

후처리

  1. customnitrogen was bubbled through
  2. addition10% Palladium on carbon (160 mg) was added
  3. filtrationthen filtered through diatomaceous earth
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customThe residue was purified by chromatography
  6. washeluting with 0-55% EtOAc/isohexane

출처 및 근거

ORD 기록
ord-b4d0eb53e10742b894d5f1644f5efc1b
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795283B2

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