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

HRID 1922591Notes

Reaction equation

HRID 1922591 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-e0afd90546574b8aa3fd188ccdedffe4
Source dataset
uspto-grants-2012_05
Patent number
US08173831B2

Reaction notes

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