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

HRID 1713858ノート

反応式

HRID 1713858 の反応式
[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

参加物

3

反応物 1

HCID 59464076Ethyl 3-(4-nitrobenzyl)cyclobutanecarboxylate

生成物 1

HCID 59464168Ethyl 3-(4-aminobenzyl)cyclobutanecarboxylate収率 50%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b4d0eb53e10742b894d5f1644f5efc1b
出典データセット
uspto-grants-2010_09
特許番号
US07795283B2

反応ノート

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