Boron Trichloride → HCID 66782856, compound

HRID 1096256Notes

Reaction equation

HRID 1096256 reaction equation
B(Cl)(Cl)Cl.[CH3:5][O:6][C:7](=[O:48])[CH:8]([N:29]1[CH2:34][CH2:33][N:32]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([O:41][C:42]([F:45])([F:44])[F:43])[CH:36]=2)[CH:31]([CH3:46])[C:30]1=[O:47])[CH2:9][CH2:10][O:11][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>C(Cl)Cl>[CH3:5][O:6][C:7](=[O:48])[CH:8]([N:29]1[CH2:34][CH2:33][N:32]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([O:41][C:42]([F:45])([F:43])[F:44])[CH:36]=2)[CH:31]([CH3:46])[C:30]1=[O:47])[CH2:9][CH2:10][OH:11]

Participants

4

Reactant 2

HCID 25135Boron Trichloride2×HCID 66783040HCID 66783040, compound

Product 1

HCID 66782856HCID 66782856, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron trichloride solution (1 M in CH2Cl2, 1.33 mL, 1.33 mmol) was added at 0° C. to a solution of 4-(tert-butyl-diphenyl-silanyloxy)-2-[3-methyl-2-oxo-4-(3-trifluoromethoxy-phenyl)-piperazin-1-yl]-butyric acid methyl ester (430 mg, 0.68 mmol) in CH2Cl2 (6 mL), then the ice bath was removed and the solution stirred for 18 h. Another portion of boron trichloride solution (1 M in CH2Cl2, 0.70 mL, 0.70 mmol) was then added, then after 6 h the reaction mixture was partitioned between CH2Cl2 and sat. aq. NaHCO3 solution. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; heptane/EtOAc 4:1) afforded the title compound (131 mg, 42%), which contained 15% of the lactonized side product, 3-methyl-1-(2-oxo-tetrahydro-furan-3-yl)-4-(3-trifluoromethoxy-phenyl)-piperazin-2-one. Light yellow oil, MS: 391.1 (M+H)+.

Workup

  1. customthe ice bath was removed
  2. customafter 6 h the reaction mixture was partitioned between CH2Cl2 and sat. aq. NaHCO3 solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-0e9f2af4595d4dae8588cb27908d6ea0
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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