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

HRID 576562Notes

Reaction equation

HRID 576562 reaction equation
[CH2:1]([N:8]([CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])C)C1C=CC=CC=1>CO.O.[OH-].[OH-].[Pd+2]>[CH3:1][NH:8][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18]

Participants

5

Reactant 1

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

Product 1

HCID 3435744N-(tert-Butoxycarbonyl)-N'-methylethylenediamineYield 94%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a flask was added 20% Pd(OH)2 on carbon (3.1 g), compound B (3.3 g, 12.5 mmol) in MeOH (200 mL) and water (10 mL), while being exposed to H2 (40 psi). After 2.5 h, the reaction mixture was filtered through celite and concentrated in vacuo. Water was then added (50 mL) and the mixture brought to pH 12 (by addition of 1 N NaOH) and extracted with DCM (3×50 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to give compound C (2.0 g, 11.7 mmol, 94%) as a colorless oil. LC-MS [M+H] 686.5 (C35H51N5O7S+H, calc: 685.9). Compound C was used without further purification.

Workup

  1. filtrationthe reaction mixture was filtered through celite and
  2. concentrationconcentrated in vacuo
  3. additionWater was then added (50 mL)
  4. additionthe mixture brought to pH 12 (by addition of 1 N NaOH)
  5. extractionextracted with DCM (3×50 mL)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-11908d6a7f994a5dad324933683da541
Source dataset
uspto-grants-2015_05
Patent number
US09040032B2

Reaction notes

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