Acetone → HCID 21186727, compound

HRID 1384288Notes

Reaction equation

HRID 1384288 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[C:5]2=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[BH4-].[Na+].CC(C)=O.[Cl-].[NH4+]>CO>[OH:13][CH:12]1[C:5]2[C:6](=[N:7][C:2]([CH3:1])=[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:4]=2)[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydride2×HCID 21186679HCID 21186679, compound

Product 1

HCID 21186727HCID 21186727, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In an atmosphere of argon, ethyl 2-methyl-5-oxo-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate (400.0 mg, 1.62 mmol) was dissolved in methanol (5.0 ml), and the solution was mixed with sodium borohydride (91.9 mg, 2.43 mmol) at 0° C. and stirred at the same temperature for 1 hour. Acetone was added dropwise to the reaction solution at 0° C. to decompose excess sodium borohydride and then the thus treated reaction solution was mixed with saturated ammonium chloride aqueous solution, extracted with ethyl acetate and washed with water and saturated brine. After drying with anhydrous sodium sulfate, the solvent was evaporated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (ether:hexane=2:1) to obtain the title compound (387.7 mg, 96.1%) as colorless oil.

Workup

  1. customthe thus treated reaction solution
  2. extractionextracted with ethyl acetate
  3. washwashed with water and saturated brine
  4. dry with materialAfter drying with anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customthe resulting residue was purified by a silica gel column chromatography (ether:hexane=2:1)

Sources & evidence

ORD record
ord-59be388bcbf34e018defb5cba54cce66
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

Loading…