Sodium Hydroxide → HCID 18187445, compound

HRID 1357917Notes

Reaction equation

HRID 1357917 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16]([F:25])([F:24])[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.I[Si](C)(C)C.C(=O)(O)[O-].[Na+].[OH-].[Na+]>C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[F:25][C:16]([F:24])([C:17]1[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=1)[CH2:15][CH2:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 18187703HCID 18187703, compound

Product 1

HCID 18187445HCID 18187445, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

1-(t-Butoxycarbonyl)-4-(3,3-difluoro-3-(4-fluorophenyl)prop-1-yl)piperidine from Step G (122 mg, 0.34 mmol) was dried by evaporation of a toluene solution at reduced pressure. The residue was dissolved in chloroform (7.6 mL) and iodotrimethylsilane (0.100 mL, 141 mg, 0.70 mmol) was added. After stirring 30 min at rt, the solution was poured into a mixture of saturated aqueous sodium bicarbonate (15 mL) and 2.5 N aq. NaOH (5 mL), and extracted with ether (50 mL). The organic layer was washed with saturated aq. brine (15 mL), dried (sodium sulfate), decanted, and evaporated to give the title compound as 88 mg of colorless oil.

Workup

  1. extractionextracted with ether (50 mL)
  2. washThe organic layer was washed with saturated aq. brine (15 mL)
  3. dry with materialdried (sodium sulfate)
  4. customdecanted
  5. customevaporated

Sources & evidence

ORD record
ord-c85ec0cc7d724a01aa0423ceda627e45
Source dataset
uspto-grants-2003_07
Patent number
US06593346B2

Reaction notes

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