Hydrochloric Acid → HCID 12988968, compound

HRID 2220097Notes

Reaction equation

HRID 2220097 reaction equation
[CH3:1][O:2][C:3]([N:5]1[CH2:10][CH:9]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:12]=2)[CH2:7][CH2:6]1)=[O:4].Cl>CO.[Pd]>[CH3:1][O:2][C:3]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:12]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 12988967HCID 12988967, compound

Product 1

HCID 12988968HCID 12988968, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-(3-Methanesulfonyl-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid methyl ester (2.0 g) was dissolved in methanol (40 ml). Concentrated hydrochloric acid (2 ml) and Pd/C (500 mg) were added. The resulting mixture was hydrogenated under a hydrogen gas pressure (50 psi) for 8 h and then filtered through a pad of celite. The solvent was evaporated in vacuum and the residue was purified by flash chromatography (CH2Cl2:MeOH, 3:1 (v/v)). Yield 0.92 g MS m/z (relative intensity, 70 eV) 297 (M+, 54), 282 (62), 238 (bp), 115 (92), 56 (93).

Workup

  1. customfor 8 h
  2. filtrationfiltered through a pad of celite
  3. customThe solvent was evaporated in vacuum
  4. customthe residue was purified by flash chromatography (CH2Cl2:MeOH, 3:1 (v/v))

Sources & evidence

ORD record
ord-4fcbe0c43cf24bcfa2440debbccb33b9
Source dataset
uspto-grants-2008_08
Patent number
US07417043B2

Reaction notes

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