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

HRID 1173959Notes

Reaction equation

HRID 1173959 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 95.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

The compound (18.0 g) obtained in Example 103-2 was dissolved in chloroform (540 ml) and then added with manganese dioxide (chemically processed product) (118 g), followed by stirring at room temperature for 15 hours. The reaction solution was filtrated through Celite and the filtrate was then concentrated under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (17.1 g) as a white solid.

Workup

  1. filtrationThe reaction solution was filtrated through Celite
  2. concentrationthe filtrate was then concentrated under reduced pressure
  3. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-f10a41520a81413699686a5687205dd6
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

Loading…