Acetic Acid → Methyl 3-bromo-5-(cyclopentylamino)benzoate

HRID 2208690ノート

反応式

HRID 2208690 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([Br:13])[CH:12]=1)[C:5]([O:7][CH2:8]C)=[O:6].[C:14]1(=O)[CH2:18][CH2:17][CH2:16][CH2:15]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[Br:13][C:11]1[CH:10]=[C:4]([CH:3]=[C:2]([NH:1][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:12]=1)[C:5]([O:7][CH3:8])=[O:6]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 8452CyclopentanoneHCID 5003444Sodium cyanoborohydrideHCID 63021768Ethyl 3-amino-5-bromobenzoate

生成物 1

HCID 70873691Methyl 3-bromo-5-(cyclopentylamino)benzoate収率 61.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a stirred solution of ethyl 3-amino-5-bromobenzoate (2 g, 8.73 mmol) and cyclopentanone (2.2 g, 26.1 mmol) in methanol (20 mL), acetic acid (1.04 g, 17.4 mmol) was added and reaction stirred at room temperature for 3 h. Then sodium cyanoborohydride (1.37 g, 21.83 mmol) was added and reaction stirred overnight. On completion, solvent was removed under reduced pressure and crude material was purified by column chromatography to afford desired compound (1.6 g, 61%).

後処理

  1. customreaction
  2. customreaction
  3. stirringstirred overnight
  4. customOn completion, solvent was removed under reduced pressure and crude material
  5. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-5d2c1e4aab074f62ba1737644f179328
出典データセット
uspto-grants-2016_06
特許番号
US09376422B2

反応ノート

読み込み中…