Hydrochloric Acid → HCID 90418937, compound

HRID 514815Notes

Reaction equation

HRID 514815 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([O:20]C(=O)C)([CH2:14][CH2:15][C:16]([F:19])([F:18])[CH3:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([CH2:14][CH2:15][C:16]([F:19])([F:18])[CH3:17])([OH:20])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90418907HCID 90418907, compound

Product 1

HCID 90418937HCID 90418937, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of tert-butyl-4-acetoxy-4-(3,3-difluorobutyl)piperidine-1-carboxylate (100 mg, 0.426 mmol) in MeOH (10 mL) and H2O (2 mL) was added NaOH (145 mg, 8.45 mmol). The resulting mixture was stirred at 40° C. for 4 h. After cooling to room temperature, the mixture was acidified with 2N HCl solution. After removal of MeOH, the resulting solution was extracted with ethyl acetate. The organic layer was dried over Na2SO4, filtered, and evaporated to dryness under reduced pressure to give the crude product which was used in the next step without further purification.

Workup

  1. temperatureAfter cooling to room temperature
  2. customAfter removal of MeOH
  3. extractionthe resulting solution was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-86af83ece4ca41ffb612a0e110576e69
Source dataset
uspto-grants-2015_08
Patent number
US09108921B2

Reaction notes

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