Ethyl Acetate → HCID 22248099, compound

HRID 914858Notes

Reaction equation

HRID 914858 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][C:13]([CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)([C:16](OCC)=[O:17])[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1.[H-].C([Al+]CC(C)C)C(C)C.O.O.O.O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+].C(OCC)(=O)C>C(OCC)C>[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:11][CH2:12][C:13]([CH2:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)([CH2:16][OH:17])[CH2:14][CH2:15]2)=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 2724148Sodium potassium tartrate tetrahydrateHCID 21225700DiisobutylaluminumhydrideHCID 22248107HCID 22248107, compound

Product 1

HCID 22248099HCID 22248099, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-20 °C

Procedure

After dissolving 247 mg of ethyl 1-(2-methoxy-3-pyridinylmethyl)-4-(2-phenylethyl)piperidine-4-carboxylate in 10 ml of diethyl ether, the solution was cooled to −20° C. and 1 ml of diisobutylaluminium hydride (1.5 M, toluene solution) was added dropwise. The mixture was stirred for 4 hours while slowly raising the temperature to room temperature, and then approximately 10 ml of a saturated aqueous solution of potassium sodium (+)-tartrate tetrahydrate and approximately 10 ml of ethyl acetate were added and the mixture was stirred for 10 minutes at room temperature. The organic layer was separated off and the aqueous layer was extracted with ethyl acetate. The organic layers were combined and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by NH silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (173 mg, 79% yield).

Workup

  1. temperaturewhile slowly raising the temperature to room temperature
  2. stirringthe mixture was stirred for 10 minutes at room temperature
  3. customThe organic layer was separated off
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by NH silica gel column chromatography (solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-33a2cf5cabce4eefad463a8256a8f772
Source dataset
uspto-grants-2007_09
Patent number
US07265108B2

Reaction notes

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