Acetone → HCID 58696292, compound

HRID 1178337Notes

Reaction equation

HRID 1178337 reaction equation
[C:1]([O:5][C:6](=[O:24])[N:7]([C@:9]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=1)([CH2:13][CH:14]=[CH2:15])[CH:10]=[N:11][CH3:12])[CH3:8])([CH3:4])([CH3:3])[CH3:2].B.[Na].CC(C)=O.O>CO>[C:1]([O:5][C:6](=[O:24])[N:7]([C@:9]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=1)([CH2:13][CH:14]=[CH2:15])[CH2:10][NH:11][CH3:12])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 58696359HCID 58696359, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 58696292HCID 58696292, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl[2-(S)-(3,4-dichlorophenyl)-1-methylimino(4-penten-2-yl)]methylcarbamate (314.5 g) was dissolved in methanol (2 L). Under cooling with ice, sodium boron hydride (38.5 g) was added thereto, and the mixture was stirred for 3 hours. Acetone (177 g) was added to the reaction mixture and then stirred for 30 minutes. The reaction mixture was poured into water, and the resultant mixture was extracted with ethyl acetate. The organic layer was sequentially washed with water and saturated brine and dried over sodium sulfate anhydrate. The solvent was concentrated under reduced pressure, and the residue was dissolved in methanol (2 L). Under cooling with ice, sodium boron hydride (16.0 g) was added thereto, and the mixture was stirred for 30 minutes. Acetone (49.2 g) was added to the reaction mixture, and the resultant mixture was stirred for 30 minutes. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was sequentially washed with water and saturated brine and dried over sodium sulfate anhydrate. The solvent was concentrated under reduced pressure, to thereby give the title compound (318.8 g). The compound was used in the next step without further purification.

Workup

  1. additionwas added
  2. stirringstirred for 30 minutes
  3. extractionthe resultant mixture was extracted with ethyl acetate
  4. washThe organic layer was sequentially washed with water and saturated brine
  5. dry with materialdried over sodium sulfate anhydrate
  6. concentrationThe solvent was concentrated under reduced pressure
  7. dissolutionthe residue was dissolved in methanol (2 L)
  8. temperatureUnder cooling with ice, sodium boron hydride (16.0 g)
  9. additionwas added
  10. stirringthe mixture was stirred for 30 minutes
  11. additionAcetone (49.2 g) was added to the reaction mixture
  12. stirringthe resultant mixture was stirred for 30 minutes
  13. additionThe reaction mixture was poured into water
  14. extractionthe mixture was extracted with ethyl acetate
  15. washThe organic layer was sequentially washed with water and saturated brine
  16. dry with materialdried over sodium sulfate anhydrate
  17. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-25a02e197c7d43618cd68b7a828340f3
Source dataset
uspto-grants-2007_10
Patent number
US07276511B2

Reaction notes

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