Hydrochloric Acid → HCID 69240668, compound

HRID 1869749Notes

Reaction equation

HRID 1869749 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]([C:15]3([C:20]([O:22][CH3:23])=[O:21])[CH2:19][CH:18]=[CH:17][CH2:16]3)[CH:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1.Cl>CO.[Pt](=O)=O>[F:24][C:2]([F:1])([F:25])[C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[CH2:14][C@@H:13]([C:15]3([C:20]([O:22][CH3:23])=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:12][CH2:11][NH:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57987540HCID 57987540, compound

Product 1

HCID 69240668HCID 69240668, compoundYield 61.4%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A mixture of the pyridine from Step 1 (270 mg, 0.77 mmol) platinum (IV) oxide (30 mg) and HCl solution (4N in dioxan, 0.2 ml, 0.8 mmol) in MeOH (15 ml) was hydrogenated at 20 psi on a Parr® apparatus for 0.5 hours. The catalyst was removed by filtration and the filtrate evaporated in vacuo. The residue was purified by chromatography on silica, eluting with 1-2% 2M NH3 in MeOH/DCM to give the title compound (168 mg, 61%) as an oil The give the desired piperidine as white solid (7.1 g, quant). M/Z (ES+) 348 (MH+). The product was contaminated with a small amount of over reduced material: M/Z (ES+) 362 (MH+).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated in vacuo
  3. customThe residue was purified by chromatography on silica
  4. washeluting with 1-2% 2M NH3 in MeOH/DCM

Sources & evidence

ORD record
ord-0a0c0554bb1e41448bb1792407e8618f
Source dataset
uspto-grants-2009_12
Patent number
US07638629B2

Reaction notes

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