Trifluoroacetic acid → HCID 18187489, compound

HRID 1862669Notes

Reaction equation

HRID 1862669 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][C:23]([F:31])([F:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:17][CH2:16]1)=O)(C)(C)C.C(=O)(O)[O-].[Na+].[OH-].[Na+]>C(Cl)Cl.O.[Cl-].[Na+].O.CCOCC>[F:31][C:23]([F:30])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:22][CH2:21][CH:18]1[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]1

Participants

9

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 18187485HCID 18187485, compound

Product 1

HCID 18187489HCID 18187489, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Trifluoroacetic acid (2.5 mL, 3.7 g, 32 mmol) was added dropwise to a solution of 1-(t-butoxycarbonyl)-4-(3,3-difluoro-3-phenylprop-1-yl)piperidine from Step C (42 mg, 0.12 mmol) in methylene chloride (2.5 mL) at 0° C. After 80 min., the solution was transferred using a double-ended needle to a rapidly stirred solution of sodium bicarbonate (5.0 g, 60 mmol) in water (50 mL). Ether (50 mL) and 2.5 N aq. NaOH (20 mL) were added, followed by solid brine to saturate the aqueous layer. The aqueous layer was separated and extracted with ether (50 mL). The organic layers were washed in succession with saturated aq. brine (20 mL), combined, dried (sodium sulfate), decanted, and evaporated to give the title compound as 27 mg of colorless oil.

Workup

  1. concentrationto saturate the aqueous layer
  2. customThe aqueous layer was separated
  3. extractionextracted with ether (50 mL)
  4. washThe organic layers were washed in succession with saturated aq. brine (20 mL)
  5. dry with materialdried (sodium sulfate)
  6. customdecanted
  7. customevaporated

Sources & evidence

ORD record
ord-c021510b80494a39812da89065a85d1a
Source dataset
uspto-grants-2003_03
Patent number
US06538002B1

Reaction notes

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