N-(2-(2-benzyloxyphenyl)ethyl)-N-methylcarbamic acid tert-butyl ester → tert-butyl N-[2-(2-hydroxyphenyl)ethyl]-N-methylcarbamate

HRID 366155Notes

Reaction equation

HRID 366155 reaction equation
[C:1]([O:5][C:6](=[O:25])[N:7]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17]CC1C=CC=CC=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:25])[N:7]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[OH:17])[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 10664950N-(2-(2-benzyloxyphenyl)ethyl)-N-methylcarbamic acid tert-butyl ester

Product 1

HCID 10848357tert-butyl N-[2-(2-hydroxyphenyl)ethyl]-N-methylcarbamateYield 82.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-(2-(2-Benzyloxyphenyl)ethyl)-N-methylcarbamic acid tert-butyl ester (4.66 g, 13.65 mmol) was dissolved in ethanol (35.6 ml) and was hydrogenated at room pressure in the presence of 10% palladium on activated carbon for 16 h. The reaction mixture was filtered through a plug of celite. The celite was washed with ethyl acetate (50 ml). The liquid phases were collected. The solvents were removed in vacuo. The crude product was purified by flash chromatography on silica (300 g), using ethyl acetate/heptane (1:2) as eluent, to give 2.84 g of N-(2-(2-hydroxyphenyl)ethyl)-N-methylcarbamic acid tert-butyl ester.

Workup

  1. filtrationThe reaction mixture was filtered through a plug of celite
  2. washThe celite was washed with ethyl acetate (50 ml)
  3. customThe liquid phases were collected
  4. customThe solvents were removed in vacuo
  5. customThe crude product was purified by flash chromatography on silica (300 g)

Sources & evidence

ORD record
ord-af5c2fb78da6404f8a684ca7920005af
Source dataset
uspto-grants-2000_10
Patent number
US06127354

Reaction notes

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