Toluene → tert-Butyl 2-(pyrrolidin-1-ylmethyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate

HRID 2388681Notes

Reaction equation

HRID 2388681 reaction equation
C1(C)C=CC=CC=1.CS(O[CH2:13][C:14]1[S:22][C:21]2[CH2:20][CH2:19][N:18]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:17][C:16]=2[CH:15]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[NH:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1>C(OCC)(=O)C>[N:36]1([CH2:13][C:14]2[S:22][C:21]3[CH2:20][CH2:19][N:18]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:17][C:16]=3[CH:15]=2)[CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 86635666tert-Butyl 2-((methylsulfonyloxy)methyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate

Product 1

HCID 86635667tert-Butyl 2-(pyrrolidin-1-ylmethyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylateYield 35%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a toluene solution (30 ml) of tert-butyl 2-((methylsulfonyloxy)methyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate (5.3 mmol) was added potassium carbonate (26.5 mmol) and pyrrolidine (6.36 mmol) and the resulting reaction mixture was refluxed for 16 h. It was cooled to 25° C., diluted with ethyl acetate and the organic layer was successively washed 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 (5% methanol in dichloromethane). Yield: 35%.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 16 h
  3. washthe organic layer was successively washed 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-6983321746584767be6fecaa2b960c65
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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