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

HRID 1525961Notes

Reaction equation

HRID 1525961 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 N3 in MeOH-DCM (0-10%) to afford tert-butyl 2-(methylamino)ethylcarbamate as a colorless oil (0.54 g, 68.3%). 1HNMR (CDCl3): δ 3.25 (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 N3 in MeOH-DCM (0-10%)

Sources & evidence

ORD record
ord-03bdb8964c444ad59295bd79ef02d613
Source dataset
uspto-grants-2015_07
Patent number
US09085527B2

Reaction notes

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