Sodium sulfate decahydrate → HCID 21186731, compound

HRID 1384289Notes

Reaction equation

HRID 1384289 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:5]2=[CH:4][C:3]=1[C:13](OCC)=[O:14].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[OH:14][CH2:13][C:3]1[CH:4]=[C:5]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:6]2=[N:7][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 62649Sodium sulfate decahydrateHCID 21186750HCID 21186750, compound

Product 1

HCID 21186731HCID 21186731, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an atmosphere of argon, ethyl 2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate (586.6 mg, 2.51 mmol) was dissolved in anhydrous THF (5.0 ml), lithium aluminum hydride THF solution (1.0 M, 5.0 ml) was added dropwise to the solution at 0° C., and the mixture was stirred at the same temperature for 2 hours. The reaction solution was mixed with sodium sulfate decahydrate at 0° C. and subjected to celite filtration. The resulting filtrate was mixed with water and extracted with ethyl acetate. The thus obtained organic layer 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=2:1) to obtain the title compound (349.5 mg, 72.8%) as white powder.

Workup

  1. filtrationsubjected to celite filtration
  2. additionThe resulting filtrate was mixed with water
  3. extractionextracted with ethyl acetate
  4. washThe thus obtained organic layer was washed with water and saturated brine in that order
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe resulting residue was purified by a silica gel column chromatography (ethyl acetate:hexane=2:1)

Sources & evidence

ORD record
ord-0eef20cc30f349b6b80d93abbf2c3d8f
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

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