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Hydrochloric Acid → 3-[5-Fluoro-3-(tetrahydro-pyran-4-yl)-pyridin-2-yloxy]-cyclobutanecarboxylic acid

HRID 1846788
Notes
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Reaction equation

HRID 1846788 reaction equation
C[O:2][C:3]([CH:5]1[CH2:8][CH:7]([O:9][C:10]2[C:15]([CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:14][C:13]([F:22])=[CH:12][N:11]=2)[CH2:6]1)=[O:4].[OH-].[Li+].Cl>CO.O>[F:22][C:13]1[CH:14]=[C:15]([CH:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[C:10]([O:9][CH:7]2[CH2:8][CH:5]([C:3]([OH:4])=[O:2])[CH2:6]2)=[N:11][CH:12]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium Hydroxide2×HCID 585486433-[5-Fluoro-3-(tetrahydro-pyran-4-YL)-pyridin-2-yloxy]-cyclobutanecarboxylic acid methyl ester

Product 1

HCID 585486643-[5-Fluoro-3-(tetrahydro-pyran-4-yl)-pyridin-2-yloxy]-cyclobutanecarboxylic acidYield 49.1%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-[5-fluoro-3-(tetrahydro-pyran-4-yl)-pyridin-2-yloxy]-cyclobutanecarboxylic acid methyl ester (3.2 g) in MeOH (60 mL) and water (15 mL) at RT was added lithium hydroxide (1.0 g, 41.6 mmol). The reaction mixture was heated to 50° C. for 2 h and then additional LiOH (400 mg) was added. Stirring was continued at 50° C. for 1 h. The reaction was neutralized with 5 M HCl and concentrated. The concentrated solution was extracted with EtOAc (50 mL) and the organic layer was washed with water (10 mL), brine (10 mL), dried over MgSO4 and concentrated to give the product (1.5 g), which was used in the next step without further purification.

Workup

  1. concentrationconcentrated
  2. extractionThe concentrated solution was extracted with EtOAc (50 mL)
  3. washthe organic layer was washed with water (10 mL), brine (10 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-974c1f8d1a8f4ec4adaea663d773b8e7
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08952037B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes