Water → HCID 117839615, compound

HRID 1477631Notes

Reaction equation

HRID 1477631 reaction equation
O1CCOCC1.O.C([O:14][C@@H:15]1[C:20]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[CH:19][CH2:18][NH:17][CH2:16]1)(=O)C(C)(C)C.O.[OH-].[Li+]>C(OCC)(=O)C>[F:27][C:24]1[CH:25]=[CH:26][C:21]([C:20]2[C@@H:15]([OH:14])[CH2:16][NH:17][CH2:18][CH:19]=2)=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 312751,4-DioxaneHCID 168937Lithium hydroxide, monohydrateHCID 117839875HCID 117839875, compound

Product 1

HCID 117839615HCID 117839615, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 1,4-dioxane (4.5 mL)-water (2.5 mL) solution of the crude product of (R)-4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridin-3-yl pivalate synthesized in Reference Synthesis Example 132, lithium hydroxide monohydrate (229 mg, 5.45 mmol) was added and the resultant mixture was stirred at 115° C. for 3 hours. After completion of the reaction, water was added to the reaction solution and extraction from the resultant mixture with ethyl acetate was performed. The organic layer was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=49/1→7/3) to obtain the title compound (640 mg, two step yield 74%).

Workup

  1. additionwas added
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=49/1→7/3)

Sources & evidence

ORD record
ord-c46c236f458f4d5ba5c582481ffad12e
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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