Hydrochloric Acid → HCID 25262108, compound

HRID 2042001Notes

Reaction equation

HRID 2042001 reaction equation
[C:1]([C:5]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:6]=1[O:7][CH2:8][CH:9]1[CH2:13][CH2:12][N:11]([C:14](=[O:21])[CH2:15][C:16]([O:18]CC)=[O:17])[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].Cl>C1COCC1>[C:1]([C:5]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:6]=1[O:7][CH2:8][CH:9]1[CH2:13][CH2:12][N:11]([C:14](=[O:21])[CH2:15][C:16]([OH:18])=[O:17])[CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59577061HCID 59577061, compound

Product 1

HCID 25262108HCID 25262108, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 3-{3-[(2-tert-butyl-4-fluorophenoxy)methyl]pyrrolidin-1-yl}-3-oxopropanoate (434 mg, 1.19 mmol) obtained in Example 214 in THF (5.0 ml) was added lithium hydroxide (1.0M aqueous solution, 5.0 mL, 5.0 mmol) at room temperature. After 3 hr, the reaction mixture was adjusted to about pH 1 with 1.0N hydrochloric acid. The obtained solution was concentrated under reduced pressure, and to the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride, dried (MgSO4), filtered, and concentrated under reduced pressure to give the title compound (392 mg, 98%) as a white solid.

Workup

  1. concentrationThe obtained solution was concentrated under reduced pressure
  2. extractionto the mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium chloride
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3cfa1459c9fc40f3977b16f30030ed34
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

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