Tetrahydrofuran → HCID 23093701, compound

HRID 1667315Notes

Reaction equation

HRID 1667315 reaction equation
C([O:5][C:6]([C:8]1[CH:13]=[C:12]([CH3:14])[C:11](/[CH:15]=[CH:16]/[CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)=[C:10]([CH3:30])[CH:9]=1)=[O:7])CCC.O1CCCC1>C(O)C.[OH-].[Na+]>[C:26]([O:25][C:23]([N:20]1[CH2:19][CH2:18][CH:17](/[CH:16]=[CH:15]/[C:11]2[C:10]([CH3:30])=[CH:9][C:8]([C:6]([OH:7])=[O:5])=[CH:13][C:12]=2[CH3:14])[CH2:22][CH2:21]1)=[O:24])([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 23093706HCID 23093706, compound

Product 1

HCID 23093701HCID 23093701, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 209 mg of tert-butyl 4-{(E)-2-[4-(butoxycarbonyl)-2,6-dimethylphenyl]vinyl}piperidine-1-carboxylate in 5 ml of ethanol, 1.5 ml of 1N aqueous sodium hydroxide solution was added, followed by stirring at ambient temperature for 3.5 hours. After 1 ml of tetrahydrofuran was added to the reaction mixture, the mixture was stirred at 50° C. overnight. The solvent was evaporated under reduced pressure, water and 1.6 ml of 1N hydrochloric acid were added thereto. The formed precipitates were collected by filtration and dried to give 179 mg of 4-{(E)-2-[1-(tert-butoxycarbonyl)piperidin-4-yl]vinyl}-3,5-dimethylbenzoic acid.

Workup

  1. stirringthe mixture was stirred at 50° C. overnight
  2. customThe solvent was evaporated under reduced pressure, water and 1.6 ml of 1N hydrochloric acid
  3. additionwere added
  4. customThe formed precipitates
  5. filtrationwere collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-31933cd66cdc4fe7b42e928310ac2f9c
Source dataset
uspto-grants-2011_10
Patent number
US08044206B2

Reaction notes

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