Toluene → HCID 68644070, compound

HRID 2388710Notes

Reaction equation

HRID 2388710 reaction equation
C1(C)C=CC=CC=1.CS(O[CH2:13][C:14]1[S:15][C:16]2[CH2:17][N:18]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:20][C:21]=2[N:22]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[NH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>C(OCC)(=O)C>[N:36]1([CH2:13][C:14]2[S:15][C:16]3[CH2:17][N:18]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:20][C:21]=3[N:22]=2)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 86635670HCID 86635670, compound

Product 1

HCID 68644070HCID 68644070, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a toluene solution (14 ml) of tert-butyl 2-((methylsulfonyloxy)methyl)-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate (2.01 mmol) was added potassium carbonate (10 mmol) and piperidine (1.1 eq.) and the resulting reaction mixture was refluxed for 16 h. It was cooled to room temperature, diluted with ethyl acetate and the organic layer was washed successively with water and brine. After drying over sodium sulfate, the organic layer was evaporated under reduced pressure to give the crude product which was purified by column chromatography (silica). Yield: 30%.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 16 h
  3. washthe organic layer was washed successively with water and brine
  4. dry with materialAfter drying over sodium sulfate
  5. customthe organic layer was evaporated under reduced pressure

Sources & evidence

ORD record
ord-12cf4edc94e84e99943a620f530edd0e
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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