Vanillylamine → HCID 15713917, compound

HRID 1805935Notes

Reaction equation

HRID 1805935 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][C:3]=1[O:10][CH3:11].[C:12]([O:16][C:17](OC([O-])=O)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(N(C(C)C)CC)(C)C>C(#N)C>[C:12]([O:16][C:17](=[O:18])[NH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([OH:1])=[C:3]([O:10][CH3:11])[CH:4]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 70966VanillylamineHCID 81531DiisopropylethylamineHCID 22064466Tert-butyldicarbonate

Product 1

HCID 15713917HCID 15713917, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-hydroxy-3-methoxybenzylamine (1.0 g, 5.27 mmol) in acetonitrile (30 mL) was added tert-butyldicarbonate (1.27 g, 5.80 mmol) and di-isopropylethylamine (1.84 mL, 10.54 mmol). The reaction was stirred at room temperature for 16 h before being partitioned between EtOAc (60 mL) and water (30 mL). The aqueous phase was separated and re-extracted with EtOAc (3×25 mL) and the combined organic extracts were washed with brine (60 mL), dried over MgSO4, filtered and concentrated. Purification by flash chromatography (40% EtOAc/hexanes) gave tert-Butyl(4-hydroxy-3-methoxybenzyl)carbamate. LCMS 275.9 (M+1)+.

Workup

  1. custombefore being partitioned between EtOAc (60 mL) and water (30 mL)
  2. customThe aqueous phase was separated
  3. extractionre-extracted with EtOAc (3×25 mL)
  4. washthe combined organic extracts were washed with brine (60 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash chromatography (40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-286d0c0e192e4912828ee87beb71c6a9
Source dataset
uspto-grants-2013_01
Patent number
US08354454B2

Reaction notes

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