(4R)-4-(4-chloro-3-nitrophenyl)pyrrolidin-2-one → (4R)-4-(3-amino-4-chlorophenyl)pyrrolidin-2-one

HRID 1799198

反応式

HRID 1799198 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][NH:11][C:10](=[O:13])[CH2:9]2)=[CH:4][C:3]=1[N+:14]([O-])=O>[Fe].C(O)(=O)C>[NH2:14][C:3]1[CH:4]=[C:5]([C@@H:8]2[CH2:12][NH:11][C:10](=[O:13])[CH2:9]2)[CH:6]=[CH:7][C:2]=1[Cl:1]

参加物

4

反応物 1

HCID 66725177(4R)-4-(4-chloro-3-nitrophenyl)pyrrolidin-2-one

生成物 1

HCID 66724932(4R)-4-(3-amino-4-chlorophenyl)pyrrolidin-2-one収率 90%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 176Acetic Acid溶媒

反応条件

温度
50 °C

実験手順

(4R)-4-(4-Chloro-3-nitrophenyl)pyrrolidin-2-one (24 g, 100 mmol) was treated with acetic acid (100 mL) and warmed to 50° C. Iron(0) (19.5 g, 350 mmol) was added in portions. After the addition, the reaction mixture was stirred for 1 h at 50° C. The mixture was then cooled and filtered through Celite. The filtrate was diluted with water and extracted with ethyl acetate (3×100 mL). The combined ethyl acetate layers were washed with water (3 times), brine, and concentrated to provide the title compound as a yellow oil. (18.9 g, 90% yield). 1H-NMR (400 MHz, CD3OD): δ 7.11-7.12 d, J=8.4 Hz, 1H), 6.73-6.74 (d, J=2.0 Hz, 1H), 6.52-6.55 (m, 1H), 3.70-3.74 (m, 1H), 3.54-3.62 (m, 1H), 3.29-3.34 (m, 1H), 2.63-2.69 (dd, J=16.4, 8.8 Hz, 1H), 2.37-2.43 (dd, J=16.4, 8.4 Hz, 1H); MS (ESI) m/z 211.07 (M+H)+.

後処理

  1. additionAfter the addition
  2. temperatureThe mixture was then cooled
  3. filtrationfiltered through Celite
  4. additionThe filtrate was diluted with water
  5. extractionextracted with ethyl acetate (3×100 mL)
  6. washThe combined ethyl acetate layers were washed with water (3 times), brine
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-b8204f05f3624f87af437cf95b05febc
出典データセット
uspto-grants-2013_01
特許番号
US08344028B2

関連ノート

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