Ethyl Acetate → HCID 57986691, compound

HRID 1615887Notes

Reaction equation

HRID 1615887 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N:11]1[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1)[C:5]([OH:7])=[O:6].[Si:18](OS(C(F)(F)F)(=O)=O)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].[CH3:33]COC(C)=O>C(Cl)Cl.N1C(C)=CC=CC=1C>[CH3:33][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([N:11]2[CH2:12][CH2:13][CH:14]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:15][CH2:16]2)=[C:2]([Cl:1])[CH:3]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 67113825HCID 67113825, compound

Product 1

HCID 57986691HCID 57986691, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 79372,6-LutidineSolvent

Procedure

To a solution of 0.70 g of 3-chloro-4-(4-hydroxypiperidino)benzoic acid in 15 ml of methylene chloride, 1.5 ml of 2,6-lutidine and 2.7 g of tert-butyldimethylsilyltriflate were added, and the mixture was stirred at room temperature for 2 weeks. To the reaction solution, EtOAc was added, and the organic layer was washed with water and brine and then dried over sodium sulfate. After the evaporation of the solvent, the obtained residue was purified by silica gel column chromatography (eluent: hexane-EtOAc=5:1˜4:1) to obtain 0.90 g of 4-(4-tert-butyldimethylsilyloxypiperidino)-3-chlorobenzoic acid methyl ester.

Workup

  1. washthe organic layer was washed with water and brine
  2. dry with materialdried over sodium sulfate
  3. customAfter the evaporation of the solvent
  4. customthe obtained residue was purified by silica gel column chromatography (eluent: hexane-EtOAc=5:1˜4:1)

Sources & evidence

ORD record
ord-926a5043da494568b68905f33f4a2e56
Source dataset
uspto-grants-2014_07
Patent number
US08765764B2

Reaction notes

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