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

HRID 919135Notes

Reaction equation

HRID 919135 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-c4ea45ba801546fa96a8766b6eeba175
Source dataset
uspto-grants-2016_03
Patent number
US09272984B2

Reaction notes

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