Water → HCID 66731515, compound

HRID 1963168Notes

Reaction equation

HRID 1963168 reaction equation
[C:1]([C:5]1[S:9][C:8]([CH:10]2[CH2:15][CH:14]([C:16]([O:18]C)=[O:17])[CH2:13][CH2:12][N:11]2[C:20]([O:22][CH3:23])=[O:21])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O.[Br-].[Li+].CC(OC)(C)C>C(#N)C>[C:1]([C:5]1[S:9][C:8]([CH:10]2[CH2:15][CH:14]([C:16]([OH:18])=[O:17])[CH2:13][CH2:12][N:11]2[C:20]([O:22][CH3:23])=[O:21])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962Water2×HCID 15413tert-Butyl methyl etherHCID 82050Lithium BromideHCID 66734916HCID 66734916, compound

Product 1

HCID 66731515HCID 66731515, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Dimethyl 2-(5-tert-butylthiophen-2-yl)piperidine-1,4-dicarboxylate (2.49 g, 7.34 mmol) was dissolved in acetonitrile (20 mL). Water (0.400 mL) and lithium bromide (5.10 g, 58.68 mmol) were added. After 5 min, TEA (4.09 mL, 29.34 mmol) was added and the reaction heated at reflux for 1 h. MTBE (150 mL) and water (150 mL) were added, shaken and the phases separated. The organic phase was extracted with water (150 mL). The combined aqueous phases were acidified with 3 M HCl to pH 1 and extracted with MTBE (2×300 mL). The combined organic phases were dried with Na2SO4, filtered and evaporated in vacuo yielding 2-(5-tert-butylthiophen-2-yl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (1.125 g, 47.1%) as a white foam. MS m/z 326 (M+H)+

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux for 1 h
  3. customthe phases separated
  4. extractionThe organic phase was extracted with water (150 mL)
  5. extractionextracted with MTBE (2×300 mL)
  6. dry with materialThe combined organic phases were dried with Na2SO4
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-e2be6a69845a4fc3bdd4d8902633312d
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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