Acetonitrile → HCID 18364725, compound

HRID 380468Notes

Reaction equation

HRID 380468 reaction equation
C([N:4]1[CH2:8][CH:7]([C:9]2[CH:13]=[CH:12][S:11][CH:10]=2)[CH:6]([CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)[CH2:5]1)C=C.CC#N>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh].O>[F:27][C:24]1[CH:25]=[CH:26][C:21]([CH:18]2[CH2:17][CH2:16][N:15]([CH2:14][CH:6]3[CH:7]([C:9]4[CH:13]=[CH:12][S:11][CH:10]=4)[CH2:8][NH:4][CH2:5]3)[CH2:20][CH2:19]2)=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 6342AcetonitrileHCID 18364713HCID 18364713, compound

Product 1

HCID 18364725HCID 18364725, compound

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 0.48 g (0.26 mmol) of 1-allyl-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(RS)-(3-thienyl)pyrrolidine and 0.067 g (0.072 mmol) of Wilkinson's catalyst [Rh(PPh)3Cl] in 20 mL of an 85% solution of CH3CN and water was heated to 90° C. and stirred for 3 h. The reaction mixture was cooled to rt and concentrated. The residue was partitioned between EtOAc and water. The organic fraction was washed with sat. NaHCO3, dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by chomatography (silica, CHCl3: MeOH: NH3, 90: 10:1) to give the title compound. 1H NMR CDCl3) δ7.28 (d of d, 1H, J=3.0, 4.8 Hz), 7.15-7.17 (m, 2H), 6.95-7.02 (m, 4H), 3.31-3.38 (m, 2H), 2.85-3.03 (m, 5H), 2.35-2.48 (m, 5H), 1.95-2.02 (m, 2H), 1.61-1.78 (m, 4H).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. concentrationconcentrated
  3. customThe residue was partitioned between EtOAc and water
  4. washThe organic fraction was washed with sat. NaHCO3
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by chomatography (silica, CHCl3: MeOH: NH3, 90: 10:1)

Sources & evidence

ORD record
ord-44cb7820520b42e9b4eb30b3d56a89c5
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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