Phenol → HCID 67543885, compound

HRID 2277075Notes

Reaction equation

HRID 2277075 reaction equation
CS([O:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)(=O)=O.[C:20]1(O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C:27]([O-:30])([O-])=[O:28].[K+].[K+].[CH3:33]N(C=O)C>>[CH3:33][O:30][C:27]([C:20]1[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=1)[O:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)=[O:28]

Participants

5

Reactant 4

HCID 996PhenolHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2765838Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate

Product 1

HCID 67543885HCID 67543885, compound

Procedure

A mixture of tert-butyl 4-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate (1.91 g, 6.51 mmol), phenol (11) (1.25 g, 8.22 mmol), K2CO3 (1.11 g, 8.03 mmol) in anhydrous DMF (10 mL) was stirred under inert atmosphere at +80° C. for 18 hrs. The reaction mixture was partitioned between aqueous 25% NH4Cl and EtOAc. Aqueous layer was extracted with EtOAc and combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated under reduced pressure to give tert-butyl 4-((3-(methoxycarbonyl)phenoxy)methyl)piperidine-1-carboxylate as a light yellow oil which was used in the next step without further purification. Yield (2.02 g, 89%).

Workup

  1. customThe reaction mixture was partitioned between aqueous 25% NH4Cl and EtOAc
  2. extractionAqueous layer was extracted with EtOAc
  3. washwere washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3dcc6565c6cd4fbcb74e1468c53c7db1
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

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