Methylamine → tert-Butyl methylcarbamate

HRID 906376Notes

Reaction equation

HRID 906376 reaction equation
[CH3:1][C:2]([O:5][C:6]([O:8]C(OC(C)(C)C)=O)=O)([CH3:4])[CH3:3].[CH3:16][NH2:17]>C(Cl)Cl>[CH3:16][NH:17][C:6](=[O:8])[O:5][C:2]([CH3:4])([CH3:3])[CH3:1]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 527635tert-Butyl methylcarbamateYield 84.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Boc anhydride (7.5 g, 34.36 mmol) in DCM (40 mL) was added methylamine (173 mL, 2M solution in THF, 345 mmol) and the reaction mixture was stirred at room temperature overnight. The solvent and excess methylamine were removed in vacuo and dilute 2M HCl (10 mL) was added. The aqueous layer was extracted with DCM (×2) and the combined organics were dried and concentrated to give the title compound as a yellow oil (3.791 g). δH (CDCl3, 400 MHz) 4.58 (1H, br.s), 2.73 (3H, d), 1.44 (9H, s).

Workup

  1. customThe solvent and excess methylamine were removed in vacuo
  2. additiondilute 2M HCl (10 mL)
  3. additionwas added
  4. extractionThe aqueous layer was extracted with DCM (×2)
  5. customthe combined organics were dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e323fe8b4557491c84f71da1dba31fbc
Source dataset
uspto-grants-2011_09
Patent number
US08012981B2

Reaction notes

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