Triethylamine → tert-butyl N-((3-hydroxyphenyl)methyl)carbamate

HRID 902661Notes

Reaction equation

HRID 902661 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][NH2:6].C(N(CC)CC)C.[O:17](C(OC(C)(C)C)=O)[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=O>CN(C=O)C>[C:21]([O:20][C:18](=[O:17])[NH:6][CH2:5][C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([OH:1])[CH:3]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 7358943-(Aminomethyl)phenol

Product 1

HCID 18369568tert-butyl N-((3-hydroxyphenyl)methyl)carbamateYield 22.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

Workup

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

Sources & evidence

ORD record
ord-76fd4b733a574e44b86d724bf907e2dc
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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