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

HRID 2080782Notes

Reaction equation

HRID 2080782 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]=[O:16])=[CH:13][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

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

Product 1

HCID 2794832tert-Butyl hydrogen ((4-formylphenyl)methyl)carbonimidateYield 116.9%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

The compound (17.6 g) obtained in Example 23-2 was dissolved in chloroform (400 ml) and then added with manganese dioxide (chemically processed product) (88.2 g) and the whole was stirred overnight at room temperature. After completion of the reaction, the resultant was filtrated through Celite. The solvent was distilled off, thereby obtaining the subject compound (20.4 g) as a colorless crystal.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe resultant was filtrated through Celite
  3. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-3b2cca34625e4bbdbe27fc39bcd2d289
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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