HCID 57656146, compound → HCID 57656316, compound

HRID 2041466Notes

Reaction equation

HRID 2041466 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])=[CH:12][C:11]=1[Cl:23])=[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])=[CH:12][C:11]=1[Cl:23])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 57656146HCID 57656146, compound

Product 1

HCID 57656316HCID 57656316, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

Add manganese dioxide (7.276 g, 83.7 mmol) to a solution of N-(tert-butoxycarbonyl)-2-chloro-4-(1-hydroxy-3,3-dimethyl-butyl)-benzylamine (1.819 g, 5.3 mmol) in anhydrous 1,4-dioxane (75 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 (85:15) to obtain the desired intermediate as a yellow oil (1.362 g, 76%).

Workup

  1. filtrationFilter the reaction mixture over Celite®
  2. concentrationconcentrate in vacuo
  3. customPurify by chromatography on silica gel eluting with hexane/EtOAc (85:15)

Sources & evidence

ORD record
ord-77d337a65d384e0d854909e664402480
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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