Ethyl 1-cyanocyclopropanecarboxylate → Ethyl 1-(aminomethyl)cyclopropanecarboxylate

HRID 1055902

反応式

HRID 1055902 の反応式
[C:1]([C:3]1([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:5][CH2:4]1)#[N:2]>[Ni].CO>[NH2:2][CH2:1][C:3]1([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:5][CH2:4]1

参加物

4

反応物 1

HCID 380810Ethyl 1-cyanocyclopropanecarboxylate

生成物 1

HCID 11480505Ethyl 1-(aminomethyl)cyclopropanecarboxylate収率 73%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 887Methanol溶媒

実験手順

In a 500-mL Parr shaker vessel, Raney nickel (750 mg) was added to MeOH (30 mL). Ethyl 1-cyanocyclopropanecarboxylate (Aldrich; 2.0 g, 14.38 mmol) was added and the resulting mixture was shaken vigorously under an H2 atmosphere (50 psi) for 24 h. The mixture was subsequently filtered through Celite, washing the Celite pad with MeOH (2×20 mL). The combined filtrates were concentrated in vacuo to provide ethyl 1-(aminomethyl)cyclopropanecarboxylate (1.5 g, 10.48 mmol, 73% yield): 1H NMR (400 MHz, CDCl3): δ 4.13 (q, 2H, J=7.2 Hz), 3.67 (s, 1H), 3.44 (s, 1H), 2.74 (br s, 2H), 1.27-1.21 (m, 5H), 0.80-0.74 (m, 2H). m/z (ESI, +ve) 144.4 (M+H)+.

後処理

  1. filtrationThe mixture was subsequently filtered through Celite
  2. washwashing the Celite pad with MeOH (2×20 mL)
  3. concentrationThe combined filtrates were concentrated in vacuo

出典と根拠

ORDレコード
ord-9fbd0ac739544c4fb347fef82b7dc619
出典データセット
uspto-grants-2016_07
特許番号
US09394297B2

関連ノート

読み込み中…