Triphenylphosphine → trans-1-Benzenesulfonyl-3-(3'-methanesulfonyl-biphenyl-3-yl)-4-phenyl-piperidine

HRID 560122Notes

Reaction equation

HRID 560122 reaction equation
[C:1]1([S:7]([N:10]2[CH2:15][CH2:14][C@@H:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@H:12]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24](Cl)[CH:23]=3)[CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:29][S:30]([C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1)(=[O:32])=[O:31].[F-].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CC(N(C)C)=O.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[C:1]1([S:7]([N:10]2[CH2:15][CH2:14][C@@H:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@H:12]([C:22]3[CH:23]=[C:24]([C:37]4[CH:36]=[CH:35][CH:34]=[C:33]([S:30]([CH3:29])(=[O:32])=[O:31])[CH:38]=4)[CH:25]=[CH:26][CH:27]=3)[CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 522689Potassium FluorideHCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 67000691trans-1-Benzenesulfonyl-3-(3-chloro-phenyl)-4-phenyl-piperidine

Product 1

HCID 67000370trans-1-Benzenesulfonyl-3-(3'-methanesulfonyl-biphenyl-3-yl)-4-phenyl-piperidineYield 26.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 21534740N,N-Dimethylacetamide--water (1/1)Solvent

Procedure

To a solution of trans-1-benzenesulfonyl-3-(3-chloro-phenyl)-4-phenyl-piperidine (150 mg) and (3-methylsulfonylphenyl)boronic acid (109 mg) in a mixture of DMA/water (2.1 mL, 20:1) was added potassium fluoride (42.3 mg), tetrakis(triphenylphosphine)palladium(0) (50.5 mg) and triphenylphoshine (22.9 mg). The reaction mixture was irradiated with microwave at 160° C. at intervals up to 80 min. Water was added, the phases were separated, and the inorganic one was extracted with diethylether (×2). The organic layers were combined, washed with brine, dried (Na2SO4) and concentrated in vacuo. Column chromatography (SiO2, n-heptane/ethyl acetate 1:1) yielded trans-1-benzenesulfonyl-3-(3′-methanesulfonyl-biphenyl-3-yl)-4-phenyl-piperidine (51 mg, 26%) as a white foam, MS: 531.5 (M+H)+.

Workup

  1. customThe reaction mixture was irradiated with microwave at 160° C. at intervals up to 80 min
  2. customthe phases were separated
  3. extractionthe inorganic one was extracted with diethylether (×2)
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-63a185513fed49bd972d66147827308a
Source dataset
uspto-grants-2011_11
Patent number
US08063088B2

Reaction notes

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