Water → HCID 117839752, compound

HRID 1477634Notes

Reaction equation

HRID 1477634 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(Cl)(Cl)Cl>[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 117839182HCID 117839182, compound

Product 1

HCID 117839752HCID 117839752, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a 1,4-dioxane (11 mL)-water (6.5 mL) solution of the crude product of (S)-4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridin-3-yl pivalate synthesized in Reference Synthesis Example 137, lithium hydroxide monohydrate (1.54 g, 36.7 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 chloroform was performed. The organic layer was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=32/1→13/7) to obtain the title compound (383 mg, two step yield 46%).

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=32/1→13/7)

Sources & evidence

ORD record
ord-b450f9dfb0064621b0db5273bc15ef3a
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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