Indole → HCID 54107065, compound

HRID 1379741Notes

Reaction equation

HRID 1379741 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CC(C)([O-])C.[K+].[CH2:16]([O:18][C:19]([N:21]1[CH2:26][CH2:25][C:24](=[CH:27]OS(C)(=O)=O)[CH2:23][CH2:22]1)=[O:20])[CH3:17]>CN(C=O)C>[CH2:16]([O:18][C:19]([N:21]1[CH2:26][CH2:25][C:24](=[CH:27][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[CH2:23][CH2:22]1)=[O:20])[CH3:17]

Participants

5

Reactant 3

HCID 798IndoleHCID 23665647Potassium tert-butoxideHCID 54001687HCID 54001687, compound

Product 1

HCID 54107065HCID 54107065, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of indole (0.53 g, 4.5 mmol) in dry DMF (15 mL) was added potassium t-butoxide (580 mg, 5.2 mmol) at ambient temperature. After stirring for 30 minutes, 4-(methanesulfonyloxymethylene)-piperidine-1-carboxylic acid ethyl ester (1.2 g, 4.5 mmol) was added. After 8 hours, the reaction mixture was quenched with water and extracted with t-butyl methyl ether (2×50 mL). The combined organic phases were washed with water (2×), dried, evaporated, and purified by column chromatography on silica gel eluting with toluene/acetone 96:4. Evaporation of the eluting solvent gave 0.92 g (71% of theory) of a slightly bluish oil.

Workup

  1. waitAfter 8 hours
  2. customthe reaction mixture was quenched with water
  3. extractionextracted with t-butyl methyl ether (2×50 mL)
  4. washThe combined organic phases were washed with water (2×)
  5. customdried
  6. customevaporated
  7. custompurified by column chromatography on silica gel eluting with toluene/acetone 96:4
  8. customEvaporation of the eluting solvent
  9. customgave 0.92 g (71% of theory) of a slightly bluish oil

Sources & evidence

ORD record
ord-742c841098554fec85366d45ab6ae408
Source dataset
uspto-grants-1997_09
Patent number
US05672618

Reaction notes

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