Triphenylphosphine → HCID 21936940, compound

HRID 1241883Notes

Reaction equation

HRID 1241883 reaction equation
FC(F)(F)S(O[C:7]1[C:12]2[CH2:13][CH2:14][CH:15]([C:19]([N:21]3[CH2:26][CH2:25][CH:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[CH3:33])[CH2:23][CH2:22]3)=[O:20])[CH2:16][C:17](=[O:18])[C:11]=2[CH:10]=[CH:9][CH:8]=1)(=O)=O.[Li+].[Cl-].[C:38]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:39]=1.C([Sn](CCCC)(CCCC)C=C)CCC>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH:38]([C:7]1[C:12]2[CH2:13][CH2:14][CH:15]([C:19]([N:21]3[CH2:22][CH2:23][CH:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[CH3:33])[CH2:25][CH2:26]3)=[O:20])[CH2:16][C:17](=[O:18])[C:11]=2[CH:10]=[CH:9][CH:8]=1)=[CH2:39]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 21936968HCID 21936968, compound

Product 1

HCID 21936940HCID 21936940, compoundYield 58.1%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

510 mg (1 mmol) of (±)-1-trifluoromethanesulfonyloxy-7-[[4-(2-methylphenyl)piperidin-1-yl]carbonyl]-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one were dissolved in 4 mL of DMF under an argon atmosphere, then 72 mg (0.1 mmol) of dichlorobis(triphenylphosphine)palladium (II), 340 mg (8 mmol) of LiCl and 105 mg (0.4 mmol) of triphenylphosphine were added, followed by a solution of 0.3 mL (1.04 mmol) of tributyl(vinyl)tin in 0.5 mL of DMF. The reaction mixture was heated to 100° C. for 6 h, then it was poured into water and extracted with AcOEt. The organic layer was dried and the solvent was removed in vacuo. The crude reaction mixture was purified by flash chromatography, eluting with a mixture AcOEt/hexane 1:1, yielding 90 mg of the title compound.

Workup

  1. extractionextracted with AcOEt
  2. customThe organic layer was dried
  3. customthe solvent was removed in vacuo
  4. customThe crude reaction mixture
  5. customwas purified by flash chromatography
  6. washeluting with a mixture AcOEt/hexane 1:1

Sources & evidence

ORD record
ord-9e648464b44e4cadba19bcace066028a
Source dataset
uspto-grants-2006_10
Patent number
US07115633B2

Reaction notes

Loading…