3-Pyridinemethanol → HCID 22054343, compound

HRID 1830248Notes

Reaction equation

HRID 1830248 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[CH3:40][O:41][C:42]1[C:43]([CH3:70])=[C:44]([C:61]([O:68][CH3:69])=[C:62]([O:66][CH3:67])[C:63]=1[O:64][CH3:65])[CH2:45][C:46]1[CH:47]=[CH:48][C:49](O)=[C:50]([CH:59]=1)[C:51]([N:53]1[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]1)=[O:52].[OH-].[Na+]>C1C=CC=CC=1>[CH3:40][O:41][C:42]1[C:43]([CH3:70])=[C:44]([C:61]([O:68][CH3:69])=[C:62]([O:66][CH3:67])[C:63]=1[O:64][CH3:65])[CH2:45][C:46]1[CH:47]=[CH:48][C:49]([O:8][CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[C:50]([CH:59]=1)[C:51]([N:53]1[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]1)=[O:52]

Participants

7

Reactant 5

HCID 75103-PyridinemethanolHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 5462977Diethyl azodicarboxylateHCID 22054317HCID 22054317, compound

Product 1

HCID 22054343HCID 22054343, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3-Pyridinemethanol (0.102 g, 0.932 mmol), triphenylphosphine (0.293 g, 1.12 mmol) and diethylazodicarboxylate (0.195 g, 1.12 mmol) were added to a benzene solution (30 ml) of N-[5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-hydroxybenzoyl]piperidine (0.320 g, 0.746 mmol) and the resulting solution was stirred at room temperature for 12 hours. The reaction solution was poured into an aqueous 2N sodium hydroxide solution (15 ml) and then extracted with methylene chloride. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by silica gel column chromatography (hexand:ethyl acetate=1.5:8.5) to obtain the titled compound (0.350 g, 0.673 mmol, 90%).

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was removed by distillation
  5. customThe obtained residue was purified by silica gel column chromatography (hexand:ethyl acetate=1.5:8.5)

Sources & evidence

ORD record
ord-4b1d10a3974c4c25be7e30616412b219
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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