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

HRID 1296215Notes

Reaction equation

HRID 1296215 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]([O:15][C:16](OC([O-])=O)=[O:17])([CH3:14])([CH3:13])[CH3:12]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][NH:6][C:16](=[O:17])[O:15][C:11]([CH3:14])([CH3:13])[CH3:12]

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 of tetrahydrofuran, and tetrahydrofuran solution (20 ml) containing 16 g of t-butyldicarbonate was added, followed by stirring for 1 hour at room temperature. The solvent was evaporated, and the residue was dissolved in ethyl acetate and successively washed with 1 N hydrochloric acid and saturated brine. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated, to give 19.0 g of t-butyl N-(2-methoxybenzyl)carbamate.

Workup

  1. additionwas added
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washsuccessively washed with 1 N hydrochloric acid and saturated brine
  5. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-cc36d635ea604f5eb39d34b499fcf0d6
Source dataset
uspto-grants-2007_07
Patent number
US07244861B2

Reaction notes

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