HCID 10782014, compound → HCID 10687516, compound

HRID 1004401Notes

Reaction equation

HRID 1004401 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([F:23])([C:14]#[C:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([F:23])([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 10782014HCID 10782014, compound

Product 1

HCID 10687516HCID 10687516, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-tert-butoxycarbonyl-4-fluoro-4-[2-(4-fluorophenyl)ethynyl]piperidine in methanol (20 ml) and glacial acid (1 ml) was hydrogenated over 10% Pd-C (0.5 g) at 50 psi for 5 hours. The catalyst was removed by filtration and the solvents removed under vacuum. The residue was dissolved in diethyl ether (20 ml) and washed with saturated aqueous sodium hydrogen carbonate (2×15 ml), dried (MgSO4) and concentrated to give the title product (430 mg, 43%) which was used in the next step without further purification; δH (360 MHz, CDCl3) 1.46 (9H, s), 1.48-1.67 (2H, m), 1.82-1.93 (4H, m), 2.68-2.73 (2H, m), 3.05-3.20 (2H, m), 3.90-3.99 (2H, m), 6.94-6.99 (2H, m), 7.11-7.15 (2H, m): m/z (ES) 326 (M+ +1).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvents removed under vacuum
  3. dissolutionThe residue was dissolved in diethyl ether (20 ml)
  4. washwashed with saturated aqueous sodium hydrogen carbonate (2×15 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9a9e2a0204074fb4afd7c35dad1329e1
Source dataset
uspto-grants-2000_04
Patent number
US06048878

Reaction notes

Loading…