tert-Butyl [4-(hydroxymethyl)benzyl]carbamate → tert-Butyl hydrogen ((4-formylphenyl)methyl)carbonimidate

HRID 1916375Notes

Reaction equation

HRID 1916375 reaction equation
[OH:1][CH2:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:5][CH:4]=1>[O-2].[O-2].[Mn+4].C(OCC)(=O)C>[CH:2]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[CH:16][CH:17]=1)=[O:1]

Participants

4

Reactant 1

HCID 2794813tert-Butyl [4-(hydroxymethyl)benzyl]carbamate

Product 1

HCID 2794832tert-Butyl hydrogen ((4-formylphenyl)methyl)carbonimidate

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To an ethyl acetate (50 mL) solution of tert-butyl [4-(hydroxymethyl)benzyl]carbamate (3.0 g), manganese dioxide (20.0 g) was added. The reaction solution was stirred at room temperature for one hour. The reaction solution was filtered through celite (trade name). The filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (n-hexane:ethyl acetate=8:2→7:3) to obtain the title compound having the following physical properties (2.3 g).

Workup

  1. filtrationThe reaction solution was filtered through celite (trade name)
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel chromatography (n-hexane:ethyl acetate=8:2→7:3)

Sources & evidence

ORD record
ord-5e513e128f2a4f848ad3e623dc66bc24
Source dataset
uspto-grants-2013_12
Patent number
US08618122B2

Reaction notes

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