Tert-butyl 2-(benzyl(methyl)amino)ethylcarbamate → N-(tert-Butoxycarbonyl)-N'-methylethylenediamine

HRID 1026859Notes

Reaction equation

HRID 1026859 reaction equation
[CH2:1]([N:8](C)[CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])C1C=CC=CC=1>[Pd].CO>[CH3:1][NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17]

Participants

4

Reactant 1

HCID 50999034Tert-butyl 2-(benzyl(methyl)amino)ethylcarbamate

Product 1

HCID 3435744N-(tert-Butoxycarbonyl)-N'-methylethylenediamineYield 68.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 2-(benzyl(methyl)amino)ethylcarbamate (1.20 g, 4.54 mmol), 10% Pd/C (0.90 g) and MeOH (60 ml) was stirred under a H2 atmosphere (0.8 MPa, RT, 16 h). The mixture was filtered and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel, eluting with saturated NH3 in MeOH-DCM (0-10%) to afford tert-butyl 2-(methylamino)ethylcarbamate as a colorless oil (0.54 g, 68.3%). 1HNMR (CDCl3): δ3.25 (m, 2H, CH2), 2.7 (m, 2H, CH2), 2.49 (s, 3H, CH3), 1.49 (s, 9H, CH3).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe crude material was purified by column chromatography on silica gel
  4. washeluting with saturated NH3 in MeOH-DCM (0-10%)

Sources & evidence

ORD record
ord-13d64e760e404edfaeee4aeaf0a0a2c8
Source dataset
uspto-grants-2014_05
Patent number
US08729293B2

Reaction notes

Loading…