tert-Butyl 2-{[3-(cyanomethyl)benzyl]oxy}ethylcarbamate → tert-Butyl 2-{[3-(2-aminoethyl)benzyl]oxy}ethylcarbamate

HRID 2228775ノート

反応式

HRID 2228775 の反応式
[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[CH2:7][O:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])#[N:2]>N.[Ni]>[NH3:2].[NH2:2][CH2:1][CH2:3][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[CH2:7][O:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:15])[CH3:16]

参加物

5

反応物 1

HCID 18470797tert-Butyl 2-{[3-(cyanomethyl)benzyl]oxy}ethylcarbamate

生成物 2

HCID 222AmmoniaHCID 18470932tert-Butyl 2-{[3-(2-aminoethyl)benzyl]oxy}ethylcarbamate収率 161.1%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 222Ammonia溶媒

実験手順

Raney® nickel (170 mg) was added to a solution of tert-butyl 2-{[3-(cyanomethyl)benzyl]oxy}ethylcarbamate (preparation 104) (654 mg, 2.26 mmol) in ethanolic ammonia solution (15 ml), and the mixture hydrogenated at 60 psi and room temperature for 24 hrs. The reaction mixture was filtered through Arbocel®, and the filtrate evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (90:10:1) to afford the title compound, (536 mg, 80%).

後処理

  1. filtrationThe reaction mixture was filtered through Arbocel®
  2. customthe filtrate evaporated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-a812d3769a7d4bc7824a5a43e3dd7ee2
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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