Ethyl Acetate → HCID 18663348, compound

HRID 1956466Notes

Reaction equation

HRID 1956466 reaction equation
Cl.[CH3:2][NH2:3].[C:4]([C:6]1[CH:19]=[CH:18][C:9]([CH2:10][N:11]2[C:15]([CH:16]=O)=[CH:14][N:13]=[CH:12]2)=[CH:8][CH:7]=1)#[N:5].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CCOC(C)=O>ClC(Cl)C>[C:4]([C:6]1[CH:19]=[CH:18][C:9]([CH2:10][N:11]2[C:15]([CH2:16][NH:3][CH3:2])=[CH:14][N:13]=[CH:12]2)=[CH:8][CH:7]=1)#[N:5]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 6364545Methylamine hydrochlorideHCID 106322894-[(5-Formylimidazol-1-yl)methyl]benzonitrile

Product 1

HCID 18663348HCID 18663348, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of methylamine hydrochloride in 5 mL dichloroethane at 0° C. are added 4 Å sieves (0.5 g), followed by 1 mmol of the aldehyde from Step E and 1.5 mmol Na(OAc)3BH. The reaction is stirred for 10 minutes at 0° C., warmed to room temperature and stirred for 2 hours. The reaction is poured into EtOAc/ sat. NaHCO3 solution. The organic layer is washed with brine, dried (Na2 SO4), filtered, and concentrated in vacuo. The crude product is taken up in 10 mL dichloromethane and 2 mL n-propylamine, stirred at room temperature for 1 hour, concentrated in vacuo , and purified by flash chromatography.

Workup

  1. additionare added 4 Å
  2. temperaturewarmed to room temperature
  3. stirringstirred for 2 hours
  4. washThe organic layer is washed with brine
  5. customdried (Na2 SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. stirring2 mL n-propylamine, stirred at room temperature for 1 hour
  9. concentrationconcentrated in vacuo
  10. custompurified by flash chromatography

Sources & evidence

ORD record
ord-8d670d490fed438a86c969a4b7d512c7
Source dataset
uspto-grants-1998_07
Patent number
US05780488

Reaction notes

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