HCID 57656530, compound → HCID 57655904, compound

HRID 911596Notes

Reaction equation

HRID 911596 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([OH:22])[CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[C:12]([Cl:23])[CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCOCC1.[O-2].[O-2].[Mn+4]>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:22])[CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[C:12]([Cl:23])[CH:11]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 57656530HCID 57656530, compound

Product 1

HCID 57655904HCID 57655904, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

Add manganese dioxide (1.096 g, 12.6 mmol) to a solution of N-(tert-butoxycarbonyl)-3-chloro-4-(1-hydroxy-3,3-dimethyl-butyl)-benzylamine (274 mg, 0.8 mmol) in anhydrous 1,4-dioxane (11.5 mL) at room temperature. Heat the mixture at 70° C. overnight. Filter the reaction mixture over Celite® and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (4:1) to obtain the desired intermediate as a yellow oil (175 mg, 64%).

Workup

  1. filtrationFilter the reaction mixture over Celite®
  2. concentrationconcentrate in vacuo
  3. customPurify by chromatography on silica gel eluting with hexane/EtOAc (4:1)

Sources & evidence

ORD record
ord-8ced88718c91462da7a22f68167e01c2
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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