tert-Butyl hydrogen {2-[benzyl(methyl)amino]ethyl}carbonimidate → N-(tert-Butoxycarbonyl)-N'-methylethylenediamine

HRID 85369

Reaktionsgleichung

Reaktionsgleichung von HRID 85369
[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]

Komponenten

4

Edukt 1

HCID 50999034tert-Butyl hydrogen {2-[benzyl(methyl)amino]ethyl}carbonimidate

Produkt 1

HCID 3435744N-(tert-Butoxycarbonyl)-N'-methylethylenediamineAusbeute 68,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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%)

Quellen und Nachweise

ORD-Eintrag
ord-7f94609dbdc24017a2276af309511796
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846972B2

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