Reaction #989843

ord-76fd4b733a574e44b86d724bf907e2dc

Reaction equation

NCc1cccc(O)c1
3-hydroxybenzylamine
CCN(CC)CC
Triethylamine
CC(C)(C)OC(=O)OC(=O)OC(C)(C)C
(BOC)2O
→
CC(C)(C)OC(=O)NCc1cccc(O)c1
titled compound
Yield 22.1%
CC(C)(C)OC(=O)NCc1cccc(O)c1
(3-Hydroxy-benzyl)-carbamic acid tert butyl ester
Yield 22.1%

Reactants

NCc1cccc(O)c1
3-hydroxybenzylamine
CCN(CC)CC
Triethylamine
CC(C)(C)OC(=O)OC(=O)OC(C)(C)C
(BOC)2O

Reagents

None

Solvents

CN(C)C=O
DMF

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    ConcentrationThe reaction was concentrated
  2. 2
    Otherchromatographed on silica gel (0 to 20% EtOAc/hexanes)

Procedure

3-hydroxybenzylamine (Apin, 1.0 g, 8.1 mmole) was dissolved in DMF(25 ml). Triethylamine (0.33 ml, 2.4 mmole) and (BOC)2O (1.8 g, 8.1 mmole) were added, the mixture stirred over night at room temperature under argon atmosphere. The reaction was concentrated, chromatographed on silica gel (0 to 20% EtOAc/hexanes) to give the titled compound (400 mg, 22%). MH+223.0

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07365085B2uspto-grants-2008_04