Dimethyl Sulfoxide → HCID 12968706, compound

HRID 1633538Notes

Reaction equation

HRID 1633538 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([C:22]2[CH:27]=[CH:26][C:25](OS(C(F)(F)F)(=O)=O)=[CH:24][CH:23]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(C)=[O:38].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:76]([O:78][CH2:79]C)C>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:76][O:78][C:79](=[O:38])[C:25]1[CH:24]=[CH:23][C:22]([C:10]2([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=3)[CH2:11][CH2:12][CH2:13][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9]2)=[CH:27][CH:26]=1

Participants

8

Reactant 5

HCID 679Dimethyl SulfoxideHCID 3283Diethyl EtherHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 12968705HCID 12968705, compound

Product 1

HCID 12968706HCID 12968706, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of trifluoro-methanesulfonic acid 4-[1-benzyl-3-(3-methoxy-phenyl)-piperidin-3-yl]-phenyl ester (12.9 g, 25.4 mmol) in a Parr pressure bottle in MeOH (39 mL) were added DMSO (18 mL) and triethylamine (21 mL, 151 mmol). To the reaction mixture were added palladium acetate (3.99 g, 17.8 mmol) and 1,3-bis (diphenylphosphino) propane (5.25 g, 12.3 mmol). The mixture was shaken under 40 psi of CO at 70° C. for 4 hours. The reaction mixture was cooled to room temperature and was diluted with diethyl ether (600 mL). The ether layer was washed with water (5×60 mL), dried (MgSO4) and concentrated. The crude residue was purified by flash chromatography with hexanes/EtOAc (3:1) to afford 9.82 g of 4-[1-benzyl-3-(3-methoxy-phenyl)-piperidin-3-yl]-benzoic acid methyl ester. 1HNMR (400 MHz, CDCl3) δ 7.87 (d, 2H), 7.41-7.20 (comp, 7H), 7.12 (t, 1H), 6.77 (s, 1H), 6.73(d, 1H) 6.66 (d, 1H), 3.86 (s, 3H), 3.71 (s, 3H), 3.51 (s, 2H), 3.05 (br, 1H), 2.68 (br, 1H), 2.55 (br, 1H), 2.41-2.24 (comp, 2H), 2.22-2.18 (m, 1H), 1.61-1.42 (comp, 2H); MS (M+1) 416.3.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe ether layer was washed with water (5×60 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude residue was purified by flash chromatography with hexanes/EtOAc (3:1)

Sources & evidence

ORD record
ord-237ba27e45c04bdba90ab4c5b4776e83
Source dataset
uspto-grants-2003_01
Patent number
US06503905B1

Reaction notes

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