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

HRID 2228729ノート

反応式

HRID 2228729 の反応式
[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]

参加物

5

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 935Nickel触媒HCID 222Ammonia溶媒HCID 702Ethanol溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-1847b5f14222421e9f368c77f58a1d3b
出典データセット
uspto-grants-2002_07
特許番号
US06417203B1

反応ノート

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