Acetone → HCID 10367750, compound

HRID 990380Notes

Reaction equation

HRID 990380 reaction equation
[NH2:1][C@@H:2]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:3]([N:5]1[CH2:10][CH2:9][N:8]([CH:11]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:7][CH2:6]1)=[O:4].[CH3:33][C:34]([CH3:36])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:18][C:15]1[CH:14]=[CH:13][C:12]([CH:11]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[N:8]2[CH2:7][CH2:6][N:5]([C:3](=[O:4])[C@@H:2]([NH:1][CH:34]([CH3:36])[CH3:33])[CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:10][CH2:9]2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 12017816HCID 12017816, compound

Product 1

HCID 10367750HCID 10367750, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-2-Amino-1-{4-[bis-(4-fluoro-phenyl)-methyl]-piperazin-1-yl}-3-phenyl-propan-1-one (0.500 g, 1.15 mmol, Example 52) and acetone (0.084 mL, 1.15 mmol) were mixed in CH2Cl2 (6 mL). After stirring at ambient temperature under nitrogen atmosphere for 30 minutes, the solution was cooled to 0° C. in an ice-water bath. To this solution was added sodium triacetoxyborohydride (0.365 g, 1.72 mmol). The resulting reaction mixture was stirred for, in succession, 30 minutes at 0° C. and 12 hours at ambient temperature. Twenty milliliters of saturated aqueous NaHCO3 solution was added to the reaction mixture, and the resulting mixture was stirred for 5 minutes. The two layers were separated and the aqueous layer was extracted with CH2Cl2 (2×20 mL). The combined organic solution was dried over Na2SO4. The solution was concentrated in vacuo affording a viscous oil. The crude product was purified by flash chromatography (1% MeOH in EtOAc) affording 460 mg (83%) of the pure titled compound as a white foam: mp 45-58° C. APCI-MS m/z 478.4 (MH+).

Workup

  1. temperaturethe solution was cooled to 0° C. in an ice-water bath
  2. customThe resulting reaction mixture
  3. stirringwas stirred for, in succession, 30 minutes at 0° C.
  4. custom12 hours
  5. customat ambient temperature
  6. stirringthe resulting mixture was stirred for 5 minutes
  7. customThe two layers were separated
  8. extractionthe aqueous layer was extracted with CH2Cl2 (2×20 mL)
  9. dry with materialThe combined organic solution was dried over Na2SO4
  10. concentrationThe solution was concentrated in vacuo
  11. customaffording a viscous oil
  12. customThe crude product was purified by flash chromatography (1% MeOH in EtOAc)

Sources & evidence

ORD record
ord-a2bfb14489404d9eb8c5f55de647a438
Source dataset
uspto-grants-2002_10
Patent number
US06458781B1

Reaction notes

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