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

HRID 2228775Notes

Reaction equation

HRID 2228775 reaction equation
[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]

Participants

5

Reactant 1

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

Product 2

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

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-a812d3769a7d4bc7824a5a43e3dd7ee2
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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