HCID 21899461, compound → HCID 21899441, compound

HRID 1986411Notes

Reaction equation

HRID 1986411 reaction equation
Br[C:2]1[S:6][C:5]([C:7]([CH3:16])([CH3:15])[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[CH3:17]>C(O)(=O)C.O.[Zn]>[CH3:16][C:7]([C:5]1[S:6][CH:2]=[C:3]([CH3:17])[CH:4]=1)([CH3:15])[C:8]([N:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:9]

Participants

5

Reactant 1

HCID 21899461HCID 21899461, compound

Product 1

HCID 21899441HCID 21899441, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of the 1-[2-(5-bromo-4-methyl-2-thienyl)-2-methylpropanoyl]pyrrolidine in acetic acid (8 ml) and water (5 ml) was added zinc dust (1.0 g, 15 mmol). The mixture was heated under reflux for 24 hours. The solvent was evaporated and the residue was dissolved in ethyl acetate and then washed sequentially with 1N hydrochloric acid, 1N sodium hydroxide and a saturated brine solution. The ethyl acetate solution was dried over magnesium sulfate and then evaporated. The residue was purified by flash chromatography on silica eluting with a 20-75% mixture of ethyl acetate in iso-hexane to afford 1-[2-methyl-2-(4-methyl-2-thienyl)propanoyl]pyrrolidine (0.151 g) as a colourless solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 24 hours
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed sequentially with 1N hydrochloric acid, 1N sodium hydroxide
  6. dry with materialThe ethyl acetate solution was dried over magnesium sulfate
  7. customevaporated
  8. customThe residue was purified by flash chromatography on silica eluting with a 20-75% mixture of ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-d6ddba9ae609453ea08277c591114efb
Source dataset
uspto-grants-2009_06
Patent number
US07547722B2

Reaction notes

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