Methylamine → tert-Butyl methylcarbamate

HRID 901855Notes

Reaction equation

HRID 901855 reaction equation
[C:1]([O:5][C:6]([O:8]C(OC(C)(C)C)=O)=O)([CH3:4])([CH3:3])[CH3:2].[CH3:16][NH2:17]>C1COCC1>[C:1]([O:5][C:6](=[O:8])[NH:17][CH3:16])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 527635tert-Butyl methylcarbamateYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of di-tert-butyldicarbonate (29.314 g, 134.27 mmol) in THF (250 ml) was cooled to 0° C. and methyl amine (71 ml, 2M in THF) was added through a funnel. After stirring at 0° C. for 2 hours, the reaction mixture was allowed to warm up to room temperature and the solvent was removed using a rotary evaporator. The resulting residue was purified by flash chromatography to give methylcarbamic-acid tert-butyl ester as a pale oil (11.518 g, 65%). 1H NMR (CDCl3, 300 MHz) δ: 2.73(d, 3H, J=4.93 Hz), 1.45(s, 9H).

Workup

  1. temperatureto warm up to room temperature
  2. customthe solvent was removed
  3. customa rotary evaporator
  4. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-8974e182be074a9db73473405dc786cf
Source dataset
uspto-grants-2008_04
Patent number
US07365063B2

Reaction notes

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