Water → HCID 21186761, compound

HRID 1384284Notes

Reaction equation

HRID 1384284 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[CH:2]=1.[H-].[Na+].Cl[CH2:12][C:13]1[N:18]=[C:17]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:16]2=[CH:15][C:14]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25].O>C1COCC1.C(OCC)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][O:8][CH2:12][C:13]2[N:18]=[C:17]3[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:16]3=[CH:15][C:14]=2[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:2]=1

Participants

7

Reactant 4

HCID 962WaterHCID 75103-PyridinemethanolHCID 24758Sodium hydrideHCID 21186683HCID 21186683, compound

Product 1

HCID 21186761HCID 21186761, compoundYield 21.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In an atmosphere of argon, 3-pyridinemethanol (0.41 ml, 4.20 mmol) was dissolved in anhydrous THF (4.0 ml), and the solution was mixed with sodium hydride (173.6 mg, 4.34 mmol) at 0° C. and stirred at the same temperature for 1 hour. To this was added dropwise THF solution (4.0 ml) of ethyl 2-chloromethyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate (1.07 g, 3.98 mmol) at 0° C., and the mixture was stirred at from 0° C. to room temperature for 20 hours. The reaction solution was diluted with ethyl acetate, mixed with water and then extracted with ethyl acetate. Thethus obtainedorganiclayer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (ethyl acetate:hexane=1:3—chloroform:methanol=40:1) to obtain the title compound (287.8 mg, 20.1%) as yellow oil.

Workup

  1. stirringthe mixture was stirred at from 0° C. to room temperature for 20 hours
  2. extractionextracted with ethyl acetate
  3. washThethus obtainedorganiclayer was washed with water and saturated brine in that order
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe resulting residue was purified by a silica gel column chromatography (ethyl acetate:hexane=1:3—chloroform:methanol=40:1)

Sources & evidence

ORD record
ord-87c9ae8f5ba44704983c4d501c1219fc
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

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