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

HRID 1816581Notes

Reaction equation

HRID 1816581 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

13.0 g of 2-methoxybenzylamine was dissolved in 80 ml tetrahydrofuran, and a solution of 16 g tertiary butyl dicarbonate in tetrahydrofuran (20 ml) was added. After the mixture was stirred at room temperature for 1 hour, the solvent was evaporated. The residue was dissolved in ethyl acetate and successively washed with 1N hydrochloricacid and brine. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated, to give 19.0 g of tertiary butyl N-(2-methoxybenzyl)carbamate was obtained.

Workup

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

Sources & evidence

ORD record
ord-ab04f5550402413f9cb8e23195bfc04d
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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