Sulfuric Acid → 1-Cyclopentyl 1-aminocyclopentanecarboxylate

HRID 1622965ノート

反応式

HRID 1622965 の反応式
[NH2:1][C:2]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.S(=O)(=O)(O)O>C1(O)CCCC1>[NH2:1][C:2]1([C:7]([O:9][CH:2]2[CH2:6][CH2:5][CH2:4][CH2:3]2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1

参加物

4

反応物 2

HCID 1118Sulfuric AcidHCID 2901Cycloleucine

生成物 1

HCID 581390221-Cyclopentyl 1-aminocyclopentanecarboxylate収率 100%

試薬・触媒・溶媒 1

HCID 7298Cyclopentanol溶媒

反応条件

温度
70 °C

実験手順

To a solution of 1-aminocyclopentanecarboxylic acid (2.58 g, 19.97 mmol) in cyclopentanol (20 ml), was added concentrated sulfuric acid (2.15 g, 21.97 mmol) and the mixture stirred overnight at 70° C. The reaction was allowed to cool to RT and the cyclopentanol removed under reduced pressure. The residue was dissolved in EtOAc (30 ml) and washed with sat. NaHCO3 (30 ml) and water (3×20 ml) then dried (MgSO4), filtered and concentrated in vacuo to leave a dark yellow oil. Purification by column chromatography (15% 1.2 M NH3/MeOH in EtOAc) afforded the desired product (1.97 g, 50% yield).

後処理

  1. temperatureto cool to RT
  2. customthe cyclopentanol removed under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc (30 ml)
  4. washwashed with sat. NaHCO3 (30 ml) and water (3×20 ml)
  5. dry with materialthen dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto leave a dark yellow oil
  9. customPurification by column chromatography (15% 1.2 M NH3/MeOH in EtOAc)

出典と根拠

ORDレコード
ord-ce05710631c14601999742a04f4a9096
出典データセット
uspto-grants-2014_07
特許番号
US08778953B2

反応ノート

読み込み中…