Aluminum → Tert-butyl-3-(4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline-6-carbonyl)azetidine-1-carboxylate

HRID 926545Notes

Reaction equation

HRID 926545 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH:12]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[N:20]=[C:19]([O:24][CH3:25])[C:18]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)=[C:17]3[Cl:37])[OH:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Al]>[O-2].[O-2].[Mn+4].O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([C:12]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[N:20]=[C:19]([O:24][CH3:25])[C:18]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)=[C:17]3[Cl:37])=[O:13])[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 5359268AluminumHCID 86715660tert-Butyl-3-((4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(hydroxy)methyl)azetidine-1-carboxylate

Product 1

HCID 86715662Tert-butyl-3-(4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline-6-carbonyl)azetidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a flask containing tert-butyl-3-((4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(hydroxy)methyl)azetidine-1-carboxylate (525 mg, 0.98 mmol, Intermediate 61: step a) was added 1,4-dioxane (40 mL) to give a homogeneous solution at room temperature. Manganese dioxide (715 mg, 8.23 mmol) was then added and the mixture was heated to 85° C. in an aluminum heating mantle under nitrogen. After 60 minutes, the contents were filtered through a Celite® pad while the solution was still warm, rinsing with THF. The effluent was concentrated and purified by passing through a short column of silica gel (10% acetone-hexane increasing to 25% acetone) to provide the title compound as a white amorphous solid.

Workup

  1. customto give a homogeneous solution at room temperature
  2. filtrationthe contents were filtered through a Celite® pad while the solution
  3. temperaturewas still warm
  4. washrinsing with THF
  5. concentrationThe effluent was concentrated
  6. custompurified

Sources & evidence

ORD record
ord-148fe19cc4d341dc9d6dabae94f8435d
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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