HCID 16737126, compound → HCID 16737128, compound

HRID 254265Notes

Reaction equation

HRID 254265 reaction equation
[C:1]1([CH:7]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:8][CH2:9][N:10]([CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][OH:21])[CH:15]=2)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[O-2].[Mn+2].C(Cl)(Cl)Cl>[C:1]1([CH:7]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:8][CH2:9][N:10]([CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]=[O:21])[CH:15]=2)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 16737126HCID 16737126, compound

Product 1

HCID 16737128HCID 16737128, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6212ChloroformSolvent

Procedure

105.2 mg (0.222 mmol, 1 eq.) of 1-(3,3-diphenylpropyl)-3-(3-hydroxymethylphenyl)-1-(2-morpholin-4-ylethyl)urea (obtained in Example 60), 6 mL of chloroform, and 193 mg (2.22 mmol, 10 eq.) of manganese oxide are introduced in succession into a 50 mL flask under an argon atmosphere while stirring. The mixture is heated under reflux for one night, then the reaction medium is filtered over Celite®. After rinsing with dichloromethane then concentrating to dryness, the crude reaction product is purified by flash chromatography over silica gel (elution gradient: CH2Cl2/AcOEt 4/1 then 1/1), leading to the desired aldehyde in a yield of 84%.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for one night
  3. filtrationthe reaction medium is filtered over Celite®
  4. washAfter rinsing with dichloromethane
  5. concentrationthen concentrating to dryness
  6. customthe crude reaction product
  7. customis purified by flash chromatography over silica gel (
  8. washelution gradient

Sources & evidence

ORD record
ord-f7b642a9827045fba7662f51cdc3c5fe
Source dataset
uspto-grants-2011_01
Patent number
US07875609B2

Reaction notes

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