Methylamine → tert-Butyl methylcarbamate

HRID 644736Notes

Reaction equation

HRID 644736 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-20d966c6f721435d8b4bad23264870b3
Source dataset
uspto-grants-2010_04
Patent number
US07700599B2

Reaction notes

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