2-Methylpropylenediamine → tert-butyl N-(2-amino-2-methylpropyl)carbamate

HRID 1631337Notes

Reaction equation

HRID 1631337 reaction equation
[C:1](=[O:14])(OC1C=CC=CC=1)[O:2][C:3]([CH3:6])([CH3:5])[CH3:4].[CH3:15][C:16]([NH2:20])([CH3:19])[CH2:17][NH2:18]>CCO>[NH2:20][C:16]([CH3:19])([CH3:15])[CH2:17][NH:18][C:1](=[O:14])[O:2][C:3]([CH3:4])([CH3:5])[CH3:6]

Participants

4

Reactant 2

HCID 131282-MethylpropylenediamineHCID 81113Carbonic acid, 1,1-dimethylethyl phenyl ester

Product 1

HCID 17909918tert-butyl N-(2-amino-2-methylpropyl)carbamateYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tert-butyl phenyl carbonate (0.421 mL, 2.270 mmol) was added to a solution of 2-methylpropane-1,2-diamine (200 mg, 2.270 mmol) in EtOH (4.5 mL) and the reaction mixture was heated at reflux overnight. The mixture was concentrated and the residue diluted in water. The mixture was acidified with 2N HCl to pH 4 and washed with DCM. The aqueous layer was treated with 1M NaOH (2 mL) and extracted with DCM. The combined organic layers were dried with MgSO4, filtered and concentrated to afford tert-butyl 2-amino-2-methylpropylcarbamate (158 mg, 37% yield) as a colorless oil. MS (apci) m/z=188.9 (M+H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux overnight
  3. concentrationThe mixture was concentrated
  4. additionthe residue diluted in water
  5. washwashed with DCM
  6. additionThe aqueous layer was treated with 1M NaOH (2 mL)
  7. extractionextracted with DCM
  8. dry with materialThe combined organic layers were dried with MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-726b54bff79443adbf9eaa8a97073f20
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

Loading…