tert-Butyl N-[3-(cyanomethyl)benzyl]-N-methylcarbamate → tert-Butyl N-[3-(2-aminoethyl)benzyl]-N-methylcarbamate

HRID 2228729노트

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HRID 2228729 반응식
[C:1]([O:5][C:6](=[O:19])[N:7]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][C:17]#[N:18])[CH:11]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]>C(O)C.N.[Ni]>[NH2:18][CH2:17][CH2:16][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[CH2:9][N:7]([CH3:8])[C:6](=[O:19])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4]

참가 물질

5

반응물 1

HCID 18470858tert-Butyl N-[3-(cyanomethyl)benzyl]-N-methylcarbamate

생성물 1

HCID 18470795tert-Butyl N-[3-(2-aminoethyl)benzyl]-N-methylcarbamate수율 78%

시약·촉매·용매 3

HCID 935Nickel촉매HCID 222Ammonia용매HCID 702Ethanol용매

실험 절차

tert-Butyl-N-[3-(cyanomethyl)benzyl]-N-methylcarbamate (preparation 14) (3 g, 11.5 mmol, slightly impure) was dissolved in ethanol saturated with NH3 (300 ml), a treated with Raney® Nickel (500 mg) and stirred under a hydrogen atmosphere (60 psi, room temperature, 18 hr). The catalyst was removed by filtration under nitrogen, the solvent evaporated to dryness and the resultant crude product purified by chromatography (SiO2, gradient elution with 100% CH2Cl2; 95:5 CH2Cl2:MeOH; 90:10 CH2Cl2:MeOH) to give the desired product (2.40 g, 78%). 1H NMR (CDCl3) δ 1.20 (s, 2H), 1.50 (s, 9H), 2.70-2.90 (m, 5H), 3.00 (s, 2H), 4.20 (s, br, 2H), 7.05 (s, br, 3H), 7.25 (s, br, 1H). LRMS m/z=265.1 (M+1)+.

후처리

  1. customThe catalyst was removed by filtration under nitrogen
  2. customthe solvent evaporated to dryness
  3. customthe resultant crude product purified by chromatography (SiO2, gradient elution with 100% CH2Cl2; 95:5 CH2Cl2:MeOH; 90:10 CH2Cl2:MeOH)

출처 및 근거

ORD 기록
ord-1847b5f14222421e9f368c77f58a1d3b
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06417203B1

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