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

HRID 1055902

반응식

HRID 1055902 반응식
[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

참가 물질

4

반응물 1

HCID 380810Ethyl 1-cyanocyclopropanecarboxylate

생성물 1

HCID 11480505Ethyl 1-(aminomethyl)cyclopropanecarboxylate수율 73%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 887Methanol용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-9fbd0ac739544c4fb347fef82b7dc619
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394297B2

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