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

HRID 567846노트

반응식

HRID 567846 반응식
[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]

참가 물질

5

반응물 1

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

생성물 2

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

시약·촉매·용매 2

HCID 935Nickel촉매HCID 222Ammonia용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-a674898ff1f34a4a9855ac236fb46c1a
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06180627B2

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