Acetonitrile → HCID 18335090, compound

HRID 842235Notes

Reaction equation

HRID 842235 reaction equation
C([N:4]1[CH2:8][CH:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:6]([CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:16][CH2:15]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:26][C:23]1[CH:22]=[CH:21][C:20]([CH:17]2[CH2:18][CH2:19][N:14]([CH2:13][CH:6]3[CH:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:8][NH:4][CH2:5]3)[CH2:15][CH2:16]2)=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 6342AcetonitrileHCID 18388397HCID 18388397, compound

Product 1

HCID 18335090HCID 18335090, compoundYield 87.2%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
90 °C

Procedure

A mixture of 1 g (2.7 mmol) of 1-allyl-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(RS)-t-butylpyrrolidine and 0.13 g (0.14 mmol) of Wilkinson's catalyst [Rh(PPh3)3Cl] in 40 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 0.75 g of the title compound.

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-2c65f1dbc5bb42a895db1db51ed5f249
Source dataset
uspto-grants-2002_04
Patent number
US06372764B1

Reaction notes

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