Hydrochloric Acid → 5,5-Dimethyl-4-(4-(methylsulfonyl)phenyl)-3-(piperidine-1-carbonyl)-5H-furan-2-one

HRID 376350Notes

Reaction equation

HRID 376350 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[Al](C)C.C([O:13][C:14]([C:16]1[C:17](=[O:33])[O:18][C:19]([CH3:32])([CH3:31])[C:20]=1[C:21]1[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=1)=O)C.Cl>C(Cl)Cl>[CH3:31][C:19]1([CH3:32])[O:18][C:17](=[O:33])[C:16]([C:14]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:13])=[C:20]1[C:21]1[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 16682925TrimethylaluminumHCID 544790785,5-Dimethyl-4-(4-(methylsulfonyl)phenyl)-2-oxo-2,5-dihydrofuran-3-carboxylic acid ethyl ester

Product 1

HCID 219484885,5-Dimethyl-4-(4-(methylsulfonyl)phenyl)-3-(piperidine-1-carbonyl)-5H-furan-2-oneYield 50.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a room temperature solution of piperidine (284 mg, 3.33 mmol) in CH2Cl2 (5 mL) was added trimethylaluminum (2M in hexane, 1.7 mL, 3.4 mmol). After 15 min, the product from Step 1 (310 mg, 0.92 mmol) was added in one portion and the mixture was heated to reflux for 20 h. The resulting solution was cooled and poured into 1M HCl (gas evolution). The organic layer was washed with brine, filtered through cotton and evaporated. Purification by flash chromatography (80% EtOAc/Hex) provided 175 mg of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 20 h
  3. temperatureThe resulting solution was cooled
  4. washThe organic layer was washed with brine
  5. filtrationfiltered through cotton
  6. customevaporated
  7. customPurification by flash chromatography (80% EtOAc/Hex)

Sources & evidence

ORD record
ord-75a63994419141e7a3350e70f33d8ee5
Source dataset
uspto-grants-2000_02
Patent number
US06020343

Reaction notes

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