2-Methoxybenzylamine → Tert-butyl (2-methoxybenzyl)carbamate

HRID 2247411Notes

Reaction equation

HRID 2247411 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].[C:11](OC([O-])=O)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][NH:6][C:11](=[O:12])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 812922-MethoxybenzylamineHCID 22064466Tert-butyldicarbonate

Product 1

HCID 22926021Tert-butyl (2-methoxybenzyl)carbamateYield 84.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Methoxybenzylamine (13.0 g) was dissolved in 80 ml of tetrahydrofuran, and then a solution of 16 g of t-butyl dicarbonate in tetrahydrofuran (20 ml) was added thereto. The mixture was stirred at room temperature for 1 hour, and then the solvent was evaporated. The residue was dissolved in ethyl acetate and successively washed with 1N hydrochloric acid and brine. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated to give 19.0 g of the title compound.

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washsuccessively washed with 1N hydrochloric acid and brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-bb8820b37b8345b7b68361b4bbabf51f
Source dataset
uspto-grants-2010_03
Patent number
US07687664B2

Reaction notes

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