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

HRID 567846Notes

Reaction equation

HRID 567846 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-a674898ff1f34a4a9855ac236fb46c1a
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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